Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

ABSTRACT

The present invention provides a novel compound that can improve the luminous efficiency, stability and life span of the element, an organic electronic element using the same, and an electronic device thereof.

BACKGROUND Technical Field

The present invention relates to compound for organic electronicelement, organic electronic element using the same, and an electronicdevice thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy by using an organicmaterial. An organic electronic element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

In the organic light emitting diode, the most problematic is thelifetime and the efficiency. As the display becomes large, theefficiency and the lifetime problem must be solved. Efficiency, lifespan, driving voltage and the like are related to each other. As theefficiency is increased, the driving voltage is relatively decreased,and as the driving voltage drops, the crystallization of the organicmaterial due to joule heating generated during driving is reduced, andas a result, the life span tends to increase.

However, simply improving the organic material layer cannot maximize theefficiency. This is because, when the optimal combination of the energylevel and T1 value between each organic material layer and the intrinsicproperties (mobility, interface characteristics, etc.) of the materialare achieved, long life and high efficiency can be achieved at the sametime.

Further, recently, in organic electroluminescent devices, in order tosolve the emission problem in the a hole transport layer, anemitting-auxiliary layer must be present between the hole transportlayer and an emitting layer, and it is necessary to develop differentemitting-auxiliary layers according to the respective emitting layers(R, G, B).

In general, electrons are transferred from the electron transport layerto the emitting layer, and holes are transferred from the hole transportlayer to the emitting layer to generate excitons by recombination.

However, the material used for the hole transport layer has a low HOMOvalue and therefore has mostly low T1 value. As a result, the excitongenerated in the emitting layer is transferred to the hole transportlayer, resulting in charge unbalance in the emitting layer, and light isemitted at the interface of the hole transport layer.

When light is emitted at the interface of the hole transport layer, thecolor purity and efficiency of the organic electronic device are loweredand the life span is shortened. Therefore, it is urgently required todevelop an emitting-auxiliary layer having a high T1 value and a HOMOlevel between the HOMO energy level of the hole transport layer and theHOMO energy level of the emitting layer.

Meanwhile, it is necessary to develop a hole injection layer materialhaving stable characteristics, that is, a high glass transitiontemperature, against joule heating generated when the device is driven,while delaying penetration of the metal oxide from the anode electrode(ITO), which is one of the causes of shortening the lifetime of theorganic electronic device, into the organic layer. The low glasstransition temperature of the hole transport layer material has acharacteristic that when the device is driven, the uniformity of thesurface of the thin film is lowered, which has been reported to have agreat influence on the lifetime of the device. In addition, OLED devicesare mainly formed by a deposition method, and it is necessary to developa material that can withstand long time in deposition, that is, amaterial having high heat resistance characteristics.

That is, in order to sufficiently exhibit the excellent characteristicsof the organic electronic element, a material for forming an organicmaterial layer in an element such as a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, an emitting-auxiliary layermaterial should be supported by stable and efficient materials. However,such a stable and efficient organic material layer material for anorganic electronic element has not been sufficiently developed yet.Therefore, development of new materials is continuously required, anddevelopment of materials for the hole transport layer or theemitting-auxiliary layer is urgently required.

PRIOR TECHNICAL LITERATURE Patent Literature

(Patent Document 0001) KR1020130076842 A

DETAILED DESCRIPTION OF THE INVENTION Summary

In order to solve the problems of the background art described above,the present invention has revealed a compound having a novel structure,and that when the compound is applied to an organic electronic element,the luminous efficiency, stability and lifetime of the element aregreatly improved.

Accordingly, it is an object of the present invention to provide a novelcompound, an organic electronic element using the same, and anelectronic device.

Technical Solution

The present invention provides a compound represented by the followingFormula (1).

In another aspect, the present invention provides an organic electricdevice including the compound represented by Formula (1) and anelectronic device thereof.

Effects of the Invention

By using the compound according to the present invention, it is possibleto achieve a high luminous efficiency, a low driving voltage, and a highheat resistance of the element, and can greatly improve the color purityand lifetime of the element.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 to FIG. 3 illustrate an example of an organic electronic elementaccording to the present invention.

FIG. 4 shows the formula according to one aspect of the presentinvention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

[24] In addition, terms, such as first, second, A, B, (a), (b) or thelike may be used herein when describing components of the presentinvention. Each of these terminologies is not used to define an essence,order or sequence of a corresponding component but used merely todistinguish the corresponding component from other component(s). Itshould be noted that if a component is described as being “connected”,“coupled”, or “connected” to another component, the component may bedirectly connected or connected to the other component, but anothercomponent may be “connected”, “coupled” or “connected” between eachcomponent.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphadic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes compound below.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup”, as used herein, means a monovalent or divalent functional group,in which R, R′ and R″ are all hydrogen in the following structures, andthe term “substituted fluorenyl group” or “substituted fluorenylenegroup” means that at least one of the substituents R, R′, R″ is asubstituent other than hydrogen, and include those in which R and R′ arebonded to each other to form a spiro compound together with the carbonto which they are bonded.

The term “spiro compound”, as used herein, has a ‘spiro union’, and aspiro union means a connection in which two rings share only one atom.At this time, atoms shared in the two rings are called ‘spiro atoms’,and these compounds are called ‘monospiro-’, ‘di-spiro-’ and‘tri-spiro-’, respectively, depending on the number of atoms in acompound.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole substituent R¹ is linked to any oneof the carbon constituting the benzene ring, when a is an integer of 2or 3, each substituent R¹s may be the same and different, when a is aninteger of 4 to 6, and is linked to the benzene ring in a similarmanner, whereas the indication of hydrogen bound to the carbon formingthe benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present inventionand an organic electronic element comprising the same will be described.

According to a specific example of the present invention, there isprovided a compound represented by Formula (1).

In Formula (1), each symbol may be defined as follows.

1) X¹, X², X³, X⁴ and X⁵ are each independently O or S,2) a, b, c and d are each independently an integer of 0 to 4, a+b+c+d is1 or more,3) e, f, g, h, i, j, k and l are each independently an integer of 0 to4,wherein in case e, f, g, h, i, j, k and l are 2 or more, R¹, R², R³, R⁴,R⁵, R⁶, R⁷ and R⁸ are each in plural being the same or different, and anadjacent plurality of R¹ or a plurality of R² or a plurality of R³ or aplurality of R⁴ or a plurality of R⁵ or a plurality of R⁶ or a pluralityof R⁷ or a plurality of R⁸ may be bonded to each other to form a ring,4) m, n, o and p are each independently an integer of 0 to 3, m+n+o+p is1 or more,5) L¹, L², L³, L⁴, L⁵, L⁶, L⁷ and L⁸ are the same or different from eachother, and are each independently selected from the group consisting ofsingle bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₂-C₆₀heterocyclic group;

wherein in case L¹, L², L³, L⁴, L⁵, L⁶, L⁷ and L⁸ are an arylene group,it is preferably an C₆˜C₃₆ arylene group, more preferably an C₆˜C₂₄arylene group, when L¹, L², L³, L⁴, L⁵, L⁶, L⁷ and L⁸ are a fused ringgroup, it is preferably a fused ring group of an C₆˜C₃₆ aliphatic ringand an C₆˜C₃₆ aromatic ring, and more preferably a fused ring group ofan C₆˜C₂₄ aliphatic ring and an C₆˜C₂₄ aromatic ring, when L¹, L², L³,L⁴, L⁵, L⁶, L⁷ and L⁸ are a heterocyclic group, it is preferably aC₂˜C₃₆ heterocyclic group, and more preferably a C₂˜C₂₄ heterocyclicgroup.

6) Ar¹, Ar³, Ar⁵ and Ar⁷ are the same or different from each other, andare each independently selected from the group consisting of hydrogen;deuterium; tritium; halogen; cyano group; nitro group; C₆-C₆₀ arylgroup; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at leastone heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀alkenyl group; C₂-C₂₀ alkynyl group; C₁-C₃₀ alkoxyl group; C₆-C₃₀aryloxy group; and -L′-N(R_(a))(R_(b));

wherein in case Ar¹, Ar³, Ar⁵ and Ar⁷ are an aryl group, it ispreferably an C₆-C₃₆ aryl group, more preferably an C₆˜C₂₅ aryl group,in case Ar¹, Ar³, Ar⁵ and Ar⁷ are an heterocyclic group, it ispreferably a C₂˜C₃₆ heterocyclic group, and more preferably a C₂˜C₂₄heterocyclic group, in case Ar¹, Ar³, Ar⁵ and Ar⁷ are a fused ringgroup, it is preferably a fused ring group of an C₆˜C₃₆ aliphatic ringand an C₆˜C₃₆ aromatic ring, more preferably a fused ring group of anC₆˜C₂₄ aliphatic ring and an C₆˜C₂₄ aromatic ring, in case Ar¹, Ar³, Ar⁵and Ar⁷ are alkyl groups, it is preferably an C₁˜C₃₆ alkyl group, morepreferably an C₁˜C₂₄ alkyl group,

7) Ar², Ar⁴, Ar⁶ and Ar⁸ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; -L⁹-Ar′;

wherein in case Ar², Ar⁴, Ar⁶ and Ar⁸ are an aryl group, it ispreferably an C₆˜C₃₆ aryl group, more preferably an C₆˜C₂₅ aryl group,in case Ar², Ar⁴, Ar⁶ and Ar⁸ are heterocyclic groups, it is preferablya C₂˜C₃₆ heterocyclic group, and more preferably a C₂˜C₂₄ heterocyclicgroup, in case Ar², Ar⁴, Ar⁶ and Ar⁸ are a fused ring group, it ispreferably a fused ring group of an C₆˜C₃₆ aliphatic ring and an C₆˜C₃₆aromatic ring, more preferably a fused ring group of an C₆˜C₂₄ aliphaticring and an C₆˜C₂₄ aromatic ring.

8) wherein L⁹ is selected from the group consisting of single bond; aC₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₂-C₆₀ heterocyclicgroup; Ar′ is selected from a C₆-C₆₀ aryl group; a fluorenylene group; aC₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S,Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring;wherein in case L⁹ is arylene group, it is preferably an C₆˜C₃₆ arylenegroup, more preferably an C₆˜C₂₄ arylene group, when L⁹ is a fused ringgroup, it is preferably a fused ring group of an C₆˜C₃₆ aliphatic ringand an C₆˜C₃₆ aromatic ring, and more preferably a fused ring group ofan C₆˜C₂₄ aliphatic ring and an C₆˜C₂₄ aromatic ring, when L⁹ is aheterocyclic group, it is preferably a C₂˜C₃₆ heterocyclic group, andmore preferably a C₂˜C₂₄ heterocyclic group.wherein in case Ar′ is an aryl group, it is preferably an C₆˜C₃₆ arylgroup, more preferably an C₆˜C₂₅ aryl group, in case Ar′ is aheterocyclic group, it is preferably C₂˜C₃₆ heterocyclic groups, andmore preferably C₂˜C₂₄ heterocyclic groups, in case Ar′ is a fused ringgroup, it is preferably a fused ring group of an C₆˜C₃₆ aliphatic ringand an C₆˜C₃₆ aromatic ring, more preferably a fused ring group of anC₆˜C₂₄ aliphatic ring and an C₆˜C₂₄ aromatic ring.9) R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are the same or different from eachother, and are each independently selected from the group consisting ofhydrogen; deuterium; tritium; halogen; cyano group; nitro group; C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including atleast one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀alkenyl group; C₂-C₂₀ alkynyl group; C₁-C₃₀ alkoxyl group; C₆-C₃₀aryloxy group; and -L′-N(R_(a))(R_(b));wherein in case R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are an aryl group, itis preferably an C₆-C₃₆ aryl group, more preferably an C₆-C₂₅ arylgroup, in case R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are an heterocyclicgroup, it is preferably a C₂˜C₃₆ heterocyclic group including at leastone heteroatom of O, N, S, Si or P; in case R¹, R², R³, R⁴, R⁵, R⁶, R⁷and R⁸ are a fused ring group, it is preferably a fused ring group of anC₆˜C₃₆ aliphatic ring and an C₆˜C₃₆ aromatic ring, more preferably afused ring group of an C₆˜C₂₄ aliphatic ring and an C₆˜C₂₄ aromaticring.10) wherein L′ is selected from the group consisting of a single bond; aC₆-C₆₀ arylene group; a fluorenylene group; C₃-C₆₀ aliphatic ring; aC₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S,Si or P; a combination thereof; wherein R_(a) and R_(b) are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; C₃-C₆₀ aliphatic ring; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P;

wherein in case L′ is an arylene group, it is preferably an C₆˜C₃₆arylene group, more preferably an C₆˜C₂₄ arylene group, in case L′ is analiphatic ring, it is preferably a C₃˜C₃₆ aliphatic ring, morepreferably C₆˜C₂₄ aliphatic ring, when L′ is a heterocyclic group, it ispreferably a C₂˜C₃₆ heterocyclic group including at least one heteroatomof O, N, S, Si or P; and more preferably a C₂˜C₂₄ heterocyclic group,wherein in case R_(a) and R_(b) are an aryl group, it is preferably anC₆˜C₃₆ aryl group, more preferably an C₆˜C₂₅ aryl group, in case R_(a)and R_(b) are an aliphatic ring, it is preferably a C₃˜C₃₆ aliphaticring, more preferably C₃˜C₂₄ aliphatic ring, in case R_(a) and R_(b) area heterocyclic group, it is preferably a C₂˜C₃₆ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; and morepreferably a C₂˜C₂₄ heterocyclic group including at least one heteroatomof O, N, S, Si or P;

11) wherein, the aryl group, arylene group, heterocyclic group,fluorenyl group, fluorenylene group, fused ring group, alkyl group,alkenyl group, alkoxy group and aryloxy group may be substituted withone or more substituents selected from the group consisting ofdeuterium; halogen; silane group; siloxane group; boron group; germaniumgroup; cyano group; nitro group; C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxylgroup; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group;C₆˜C₂₅ aryl group; C₆-C₂₅ aryl group substituted with deuterium; afluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group;C₇-C₂₀ arylalkyl group; C₈-C₂₀ arylalkenyl group; and-L′-N(R_(a))(R_(b)); the substituents may combine each other to form asaturated or unsaturated ring selected from the group consisting of aC₃-C₆₀ aliphatic ring, a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclicgroup, a fused ring formed by combination thereof.

Also, Formula 1 includes a compound represented by any one of Formulas1-1 to 1-9 below.

In Formulas 1-1 to 1-9,

X¹, X², X³, X⁴, X⁵ and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and L¹, L², L³,L⁴, L⁵, L⁶, L⁷, L⁸ and e, f, g, h, i, j, k, l, m, n, o and p are thesame defined in Formula 1.

Also, Formula 1 includes a compound represented by Formula 2 below.

In Formula 2,

X¹, X², X³, X⁴, X⁵ and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and L¹, L², L³,L⁴, L⁵, L⁶, L⁷, L⁸ and Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, and Ar⁸, anda, b, c, d, e, f, g, h, i, j, k, l and n are the same defined in Formula1.

Formula 1 includes a compound represented by any one of Formulas 2-1 to2-4 below.

In Formulas 2-1 to 2-4,

X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, Ar³, Ar⁴, e, f, g, h, j and n arethe same as defined in Formula 1.

Formula 1 includes a compound represented by Formula 3 below.

In Formula 3,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, Ar⁴, e, f, g, h

j are the same as defined in Formula 1,2) Ar^(3a) is selected from the group consisting of deuterium; tritium;halogen; cyano group; nitro group; C₆-C₆₀ aryl group; a fluorenyl group;a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N,S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynylgroup; C₁-C₃₀ alkoxyl group; C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b));

Formula 1 includes a compound represented by Formula 4 below.

In Formula 4, each symbol may be defined as follows.

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, L⁹, Ar³, e, f, g, h, j and n arethe same as defined in Formula 1,2) X⁶ and X⁷ are each independently a single bone, CR′R″, O or S,

However, except when X⁶ and X⁷ are a single bond at the same time,

3) R′ and R″ are each independently a hydrogen; C₆-C₆₀ aryl group; afluorenyl group; a C₃-C₆₀ heterocyclic group; C₁-C₆₀ alkyl group; C₂-C₆₀alkenyl group; or C₆-C₆₀ aryloxy group; R′ and R″ are bonded to eachother to form a C₆-C₆₀ aromatic ring; fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; C₃-C₆₀ aliphatic ring; or a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring.wherein in case R′ and R″ are an aryl group, it is preferably an C₆˜C₃₆aryl group, more preferably an C₆˜C₂₅ aryl group, in case R′ and R″ area heterocyclic group, it is preferably C₂˜C₃₆ heterocyclic groups, andmore preferably C₂˜C₂₄ heterocyclic groups, in case R′ and R″ are analkyl group, it is preferably C₁-C₃₆ alkyl group, and more preferablyC₁-C₂₄ alkyl group, in case R′ and R″ are an alkenyl group, it ispreferably a C₂-C₃₆ alkenyl group, and more preferably a C₂-C₂₄ alkenylgroup, in case R′ and R″ are an aryloxy group, it is preferably C₆-C₃₆aryloxy group, and more C₆-C₂₄ aryloxy group.4) R⁹ and R¹⁰ are the same as the definition of R¹ in Formula 1,5) q is an integer of 0 to 3, r is an integer of 0 to 4,

Formula 1 includes a compound represented by Formula 4-1 below.

In Formula 4-1,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, L⁹, Ar³, e, f, g, h, j and n arethe same as defined in Formula 1,2) R⁹, R¹⁰, R′, R″, q and r are the same as defined in Formula 4,3) Z is a single bond, 0 or S.

Formula 1 includes a compound represented by Formula 4-2 below.

In Formula 4-2,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, L⁹, Ar³, e, f, g, h, j and n arethe same as defined in Formula 1,2) R⁹, R¹⁰, R′, R″, q and r are the same as defined in Formula 4,

Formula 1 includes a compound represented by any one of Formulas 5-1 to5-4 below.

In Formulas 5-1 to 5-4,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, Ar³, e, f, g, h, j and n are thesame as defined in Formula 1,2) R⁹, R¹⁰, R′, R″, q and r are the same as defined in Formula 4,

Formula 1 includes a compound represented by Formula 6-1 below.

In Formula 6-1,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, L⁹, Ar³, e, f, g, h, j and n arethe same as defined in Formula 1,2) R⁹, R¹⁰, q and r are the same as defined in Formula 4,

3) Y¹ is O or S,

4) R¹¹ and R¹² are the same as the definition of R¹ in Formula 1,5) s and t are each independently an integer of 0 to 4.

Formula 1 includes a compound represented by Formula 6-2 below.

In Formula 6-2,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, Ar³, e, f, g, h, j and n are thesame as defined in Formula 1,2) R⁹, R¹⁰, q and r are the same as defined in Formula 4,3) Y¹, R¹¹, R¹², s and t are the same as defined in Formula 6-1.

Formula 1 includes a compound represented by Formula 6-3 below.

In Formula 6-3,

1) X¹, X³, R¹, R², R³, R⁴, R⁶, L³, L⁴, Ar³, e, f, g, h, j and n are thesame as defined in Formula 1,2) R⁹, R¹⁰, q and r are the same as defined in Formula 4,3) Y¹, R¹¹, R¹², s and t are the same as defined in Formula 6-1.

Specifically, the compound represented by Formula 1 may be a compoundrepresented by any one of the following compounds P-1 to P-139, but isnot limited thereto.

Further, specifically, the compound represented by Formula 1 may be acompound represented by any one of the following compounds P1-1 toP1-86, but is not limited thereto.

Also, specifically, the compound represented by Formula 1 may be acompound represented by any one of the following compounds P2-1 toP2-55, but is not limited thereto.

Referring to FIG. 1, the organic electronic element (100) according tothe present invention includes a first electrode (110), a secondelectrode (170), an organic material layer comprising single compoundrepresented by Formula 1 or 2 or more compounds between the firstelectrode (110) and the second electrode (170), Here, the firstelectrode (110) may be an anode or a positive electrode, and the secondelectrode (170) may be a cathode or a negative electrode. In the case ofan inverted organic electronic element, the first electrode may be acathode, and the second electrode may be an anode.

The organic material layer may sequentially include a hole injectionlayer (120), a hole transport layer (130), an emitting layer (140), anelectron transport layer (150), and an electron injection layer (160)formed in sequence on the first electrode (110). Here, the remaininglayers except the emitting layer (140) may not be formed. The organicmaterial layer may further include a hole blocking layer, an electronblocking layer, an emitting-auxiliary layer (220), a buffer layer (210),etc., and the electron transport layer (150) and the like may serve as ahole blocking layer. (see FIG. 2)

Also, the organic electronic element according to an embodiment of thepresent invention may further include a protective layer or a lightefficiency enhancing layer (180). The light efficiency enhancing layermay be formed on a surface not in contact with the organic materiallayer among both surfaces of the first electrode or on a surface not incontact with the organic material layer among both surfaces of thesecond electrode. The compound according to an embodiment of the presentinvention applied to the organic material layer may be used as amaterial for a hole injection layer (120), a hole transport layer (130),an emitting-auxiliary layer (220), an electron transport auxiliarylayer, an electron transport layer (150), an electron injection layer(160), a host or dopant of an emitting layer (140) or the lightefficiency enhancing layer. Preferably, for example, the compoundaccording to Formula 1 of the present invention may be used as amaterial for the emitting-auxiliary layer.

The organic material layer may include 2 or more stacks including a holetransport layer, an emitting layer, and an electron transport layersequentially formed on the anode, and may further include a chargegeneration layer formed between the 2 or more stacks (see FIG. 3).

Otherwise, even if the same core is used, the band gap, the electricalcharacteristics, the interface characteristics, and the like may varydepending on which substituent is bonded at which position, thereforethe choice of core and the combination of sub-substituents associatedtherewith is also very important, and in particular, when the optimalcombination of energy levels and T1 values and unique properties ofmaterials (mobility, interfacial characteristics, etc.) of each organicmaterial layer is achieved, a long life span and high efficiency can beachieved at the same time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, a metal or a metal oxide havingconductivity or an alloy thereof is deposited on a substrate to form acathode, and the organic material layer including the hole injectionlayer (120), the hole transport layer (130), the emitting layer (140),the electron transport layer (150), and the electron injection layer(160) is formed thereon, and then depositing a material usable as acathode thereon can manufacture an organic electroluminescent deviceaccording to an embodiment of the present invention.

Also, the present invention provides the organic electronic elementwherein the organic material layer is formed by one of a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process or a roll-to-roll process, andthe organic material layer provides an organic electronic elementcomprising the compound as an electron transport material.

As another specific example, the present invention provides an organicelectronic element that is used by mixing the same or differentcompounds of the compound represented by Formula 1 to the organicmaterial layer.

In another aspect, the present invention provides an emitting-auxiliarylayer composition comprising a compound represented by Formula 1, andprovides an organic electronic element comprising the emitting-auxiliarylayer.

The present invention also provides an electronic device comprising adisplay device including the organic electronic element; and a controlunit for driving the display device.

According to another aspect, the present invention provides an displaydevice wherein the organic electronic element is at least one of anOLED, an organic solar cell, an organic photo conductor, an organictransistor (organic TFT) and an element for monochromic or whiteillumination. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula 1of the present invention and preparation examples of the organicelectronic element of the present invention will be described in detailby way of example, but are not limited to the following examples.

Synthesis Example 1

The compound (Final product) represented by Formula 1 according to thepresent invention may be prepared by reacting as in Scheme 1 below, butis not limited thereto.

In Reaction Scheme 1,

1) X¹, X², X³, X⁴, X⁵, R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸, L¹, L², L³,L⁴, L⁵, L⁶, L⁷ and L⁸, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, and Ar⁸, and ato P are the same as defined above,2) Hal¹ to Hal⁴ are each independently Br or Cl,3) a′ to d′ are each independently 0 or 1, at least one of a′ to d′ is1,4) Y is the same as the definition of X¹, X², X³, X⁴, X⁵,5) Ar¹′ is the same as the definition of Ar¹, Ar³, Ar⁵ or Ar⁷,6) Ar²′ is the same as the definition of Ar³, Ar⁴, Ar⁶ or Ar⁸,7) R^(1′) is the same as the definition of R⁵, R⁶, R⁷, R⁸8) L¹′ is the same as the definition of L², L⁴, L⁶ or L⁸,9) e′ is an integer of 0 to 3, f′ is an integer of 0 to 4.

I. Synthesis of Sub 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction path ofScheme 2 below, but is not limited thereto. When X¹ is —OH, thesynthesis path of (1) of Reaction Scheme 2 is followed, and when X¹ is—SH, the synthesis path of (2) of Reaction Scheme 2 is followed.

In Reaction Scheme 2,

X¹, R¹, R², R³, R⁴, e, f, g, h, Hal¹, Hal², Hal³, Hal⁴ and a′, b′, c′,d′ are the same as defined in Formula 1.

Synthesis examples of specific compounds belonging to Sub 1 are asfollows.

1. Synthesis Example of Sub 1-1

(1) Synthesis Example of Sub 1-1-a

5-chloro-2-iodobenzoic acid (50.0 g, 177 mmol), Phenol (33.3 g, 354mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (80.9 g, 531 mmol),pyridine (2.9 mL), Copper powder (1.5 g, 23 mmol), CuI (1.5 g, 7.97mmol) were placed in a round bottom flask, and DMF (1.2 L) was added,followed by refluxing for 3 hours. When the reaction is complete, coolto room temperature and add 3M HCl until precipitation is complete.Thereafter, the precipitate was washed with water and dried to obtain38.3 g (yield 87%) of the product.

(2) Synthesis Example of Sub 1-1-b

Sub 1-1-a (38.3 g, 154 mmol) obtained in the above synthesis was addedto a round bottom flask, and H₂SO₄ (1.1 mL, 21.5 mmol) was added,followed by refluxing until all the starting materials were dissolved.When all the starting materials are dissolved, cool to room temperatureand add ice water to precipitate. Thereafter, the precipitate was washedwith water, dried, dissolved in CH₂Cl₂, and recrystallized with aSilicagel column to obtain 23.09 g (yield 65%) of the product.

(3) Synthesis Example of Sub 1-1-c

2-bromo-1,1′-biphenyl (23.3 g, 99.7 mmol) was dissolved in THF (270 mL)in a round bottom flask under a nitrogen atmosphere, and then cooled to−78° C.

Then, n-BuLi (40 mL) was slowly titrated and the mixture was stirred for30 minutes. Subsequently, Sub1-1-b (23 g, 99.7 mmol) obtained in theabove synthesis was dissolved in THF (140 mL), and then slowly titratedinto a reaction round bottom flask. After stirring for an additional 1hour at −78° C., it is gradually raised to room temperature. When thereaction was completed, the product was extracted with Ethyl acetate andwater, and the organic layer was dried over MgSO₄ and concentrated, andthe resulting compound was recrystallized in a silicagel column toobtain 32.6 g (yield 85%) of the product.

(4) Synthesis Example of Sub 1-1

Sub 1-1-c (32 g, 84.7 mmol) obtained in the above synthesis, acetic acid(208 mL), and concentrated hydrochloric acid (34.6 mL) were added to around bottom flask, followed by stirring at 60 to 80° C. for 3 hoursunder a nitrogen atmosphere. When the reaction was completed, theproduct was extracted with CH₂Cl₂ and water, and the organic layer wasdried over MgSO₄ and concentrated, and the resulting compound wasrecrystallized with a silicagel column to obtain 27.7 g (91% yield) ofthe product.

2. Synthesis Example of Sub 1-11

(1) Synthesis Example of Sub 1-11-a

2-iodobenzoic acid (50.0 g, 202 mmol), Thiophenol (22.2 g, 202 mmol),Potassium hydroxide (56.6 g, 1008 mmol), Copper powder (1.3 g, 20.2mmol) were placed in a round bottom flask and water (1.3 L) was added,followed by refluxing for 12 hours. When the reaction is complete, coolto room temperature and add 3M HCl until precipitation is complete.Thereafter, the precipitate was washed with water and dried to obtain41.3 g (yield 89%) of the product.

(2) Synthesis Example of Sub 1-11-b

Sub 1-11-a (41.3 g, 179 mmol) and H₂SO₄ (1.3 mL) obtained in the abovesynthesis was used for the synthesis of Sub 1-1-b to obtain 25.9 g (68%yield) of a product.

(3) Synthesis Example of Sub 1-11-c

2-bromo-4′-chloro-1,1′-biphenyl (32.6 g, 122 mmol), n-BuLi (49 mL), Sub1-11-b (25.9 g, 122 mmol) obtained in the above synthesis was used forthe synthesis of Sub 1-1-c to obtain 40.1 g (82% yield) of a product.

(4) Synthesis Example of Sub 1-11

Sub 1-11-c (40.1 g, 100 mmol) obtained in the above synthesis, aceticacid (250 mL), and concentrated hydrochloric acid (40 mL) were obtainedby using the synthesis method of Sub 1-1 above to obtain 31.8 g (yield83%) of the product.

3. Synthesis Example of Sub 1-20

(1) Synthesis Example of Sub 1-20-a

3-chloro-2-iodobenzoic acid (30.0 g, 106.2 mmol), Thiophenol (11.7 g,106.2 mmol), Potassium hydroxide (29.8 g, 531 mmol), Copper powder (0.67g, 10.6 mmol) were used to obtain 23.6 g of a product (84% yield) usingthe synthesis method of Sub 1-11-a.

(2) Synthesis Example of Sub 1-20-b

Sub 1-20-a (23.6 g, 89.2 mmol) and H₂SO₄ (0.67 mL) obtained in the abovesynthesis was used for the synthesis of Sub 1-1-b to obtain 14.5 g (66%yield) of a product.

(3) Synthesis Example of Sub 1-20-c

1-(2-bromophenyl)naphthalene (16.6 g, 58.8 mmol), n-BuLi (24 mL),Sub1-20-b (14.5 g, 58.8 mmol) obtained in the above synthesis was usedfor the synthesis of Sub 1-1-c to obtain 21.5 g (81% yield) of aproduct.

(4) Synthesis Example of Sub 1-20

Sub 1-20-c (21 g, 46.6 mmol) obtained in the above synthesis, aceticacid (116 mL), and concentrated hydrochloric acid (19 mL) were obtainedby using the synthesis method of Sub 1-1 above to obtain 15.9 g (yield79%) of the product.

4. Synthesis Example of Sub 1-55

(1) Synthesis Example of Sub 1-55-a

2-iodobenzoic acid (15 g, 60.5 mmol), Sub1′-55 (37.9 g, 120.1 mmol),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (27.6 g, 181.4 mmol), pyridine(0.98 mL), Copper powder (0.5 g, 7.9 mmol), CuI (0.5 g, 2.7 mmol) wereused to obtain 27.7 g of a product (78% yield) using the synthesismethod of Sub 1-1-a.

(2) Synthesis Example of Sub 1-55-b

Sub 1-55-a (27.7 g, 47.1 mmol) and H₂SO₄ (0.35 mL) obtained in the abovesynthesis was used for the synthesis of Sub 1-1-b to obtain 17.7 g (64%yield) of a product.

(3) Synthesis Example of Sub 1-55-c

2-bromo-2′-chloro-1,1′-biphenyl (7.8 g, 29 mmol), n-BuLi (11.7 mL), Sub1-55-b (17 g, 29 mmol) obtained in the above synthesis was used for thesynthesis of Sub 1-1-c to obtain 17.3 g (77% yield) of a product.

(4) Synthesis Example of Sub 1-55

Sub 1-55-c (17.3 g, 22.3 mmol) obtained in the above synthesis, aceticacid (56 mL), and concentrated hydrochloric acid (9.3 mL) were obtainedby using the synthesis method of Sub 1-1 above to obtain 13.5 g (yield80%) of the product.

5. Synthesis Example of Sub 1-140

(1) Synthesis Example of Sub 1-140-a

3-chloro-2-iodobenzoic acid (18 g, 63.7 mmol), Sub1′-140 (28.3 g, 63.7mmol), Potassium hydroxide (17.9 g, 318.6 mmol), Copper powder (0.4 g,6.4 mmol) were used to obtain 30.1 g of a product (79% yield) using thesynthesis method of Sub 1-11-a.

(2) Synthesis Example of Sub 1-140-b

Sub 1-140-a (30.1 g, 46.3 mmol) and H₂SO₄ (0.35 mL) obtained in theabove synthesis was used for the synthesis of Sub 1-1-b to obtain 18.1 g(62% yield) of a product.

(3) Synthesis Example of Sub 1-140-c

Sub1″-140 (19.9 g, 30.3 mmol), n-BuLi (12.2 mL), Sub1-141-b (18.1 g,30.3 mmol) obtained in the above synthesis were used for the synthesisof Sub 1-1-c to obtain 24.5 g (70% yield) of a product.

(4) Synthesis Example of Sub 1-140

Sub 1-140-c (24.5 g, 21.1 mmol) obtained in the above synthesis, aceticacid (53 mL), and concentrated hydrochloric acid (8.8 mL) were obtainedby using the synthesis method of Sub 1-1 above to obtain 18.1 g (yield75%) of the product.

6. Synthesis Example of Sub 1-152

(1) Synthesis Example of Sub 1-152-a

4-chloro-2-iodobenzoic acid (12 g, 42.5 mmol), 3-chlorophenol (10.9 g,84.97 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (19.4 g, 127.5mmol), pyridine (0.69 mL), Copper powder (0.35 g, 5.5 mmol), CuI (0.36g, 1.9 mmol) were used to obtain 9.7 g of a product (81% yield) usingthe synthesis method of Sub 1-1-a.

(2) Synthesis Example of Sub 1-152-b

Sub 1-152-a (9.7 g, 34.3 mmol) and H₂SO₄ (0.26 mL) obtained in the abovesynthesis was used for the synthesis of Sub 1-1-b to obtain 6.6 g (73%yield) of a product.

(3) Synthesis Example of Sub 1-152-b′

The obtained Sub 1-152-b (6.6 g, 24.9 mmol), Sub 2-20 (17.5 g, 49.8mmol), Pd₂(dba)₃ (0.68 g, 0.75 mmol), P(t-Bu)₃ (50 wt % Sol.) (0.6 mL,1.5 mmol), t-BuONa (7.18 g, 74.7 mmol) were added to anhydrous Toluene(150 mL) and reacted for 3 hours. After confirming the completion of thereaction, extraction was performed with CH₂Cl₂ and water, and theorganic layer was dried over MgSO4 and concentrated. The resultingcompound was silicagel column and recrystallized to give a product 14.8g (yield 60%).

(4) Synthesis Example of Sub 1-152-c

Sub 1″-152 (8.97 g, 14.9 mmol), n-BuLi (6 mL), Sub 1-152-b′ (14.8 g,14.9 mmol) obtained in the above synthesis was used to obtain a product14.0 g (62% yield) using the synthesis method of Sub 1-1-c.

(5) Synthesis Example of Sub 1-152

Sub 1-152-c (14 g, 9.3 mmol) obtained in the above synthesis, aceticacid (23 mL), and concentrated hydrochloric acid (3.8 mL) were used toobtain 8.7 g (63% yield) of the product using the synthesis method ofSub 1-1.

Meanwhile, the compound belonging to Sub 1 may be the followingcompound, but is not limited thereto, and Table 1 shows FD-MS (FieldDesorption-Mass Spectrometry) values of the compound belonging to Sub 1.

TABLE 1 compound FD-MS compound FD-MS Sub1-1 m/z = 366.08(C₂₅H₁₅ClO =366.84) Sub1-2 m/z = 366.08(C₂₅H₁₅ClO = 366.84) Sub1-3 m/z =366.08(C₂₅H₁₅ClO = 366.84) Sub1-4 m/z = 366.08(C₂₅H₁₅ClO = 366.84)Sub1-5 m/z = 366.08(C₂₅H₁₅ClO = 366.84) Sub1-6 m/z = 366.08(C₂₅H₁₅ClO =366.84) Sub1-7 m/z = 366.08(C₂₅H₁₅ClO = 366.84) Sub1-8 m/z =366.08(C₂₅H₁₅ClO = 366.84) Sub1-9 m/z = 382.06(C₂₅H₁₅ClS = 382.91)Sub1-10 m/z = 382.06(C₂₅H₁₅ClS = 382.91) Sub1-11 m/z = 382.06(C₂₅H₁₅ClS= 382.91) Sub1-12 m/z = 382.06(C₂₅H₁₅ClS = 382.91) Sub1-13 m/z =382.06(C₂₅H₁₅ClS = 382.91) Sub1-14 m/z = 382.06(C₂₅H₁₅ClS = 382.91)Sub1-15 m/z = 382.06(C₂₅H₁₅ClS = 382.91) Sub1-16 m/z = 382.06(C₂₅H₁₅ClS= 382.91) Sub1-17 m/z = 432.07(C₂₉H₁₇ClS = 432.97) Sub1-18 m/z =432.07(C₂₉H₁₇ClS = 432.97) Sub1-19 m/z = 432.07(C₂₉H₁₇ClS = 432.97)Sub1-20 m/z = 432.07(C₂₉H₁₇ClS = 432.97) Sub1-21 m/z = 442.11(C₃₁H₁₉ClO= 442.94) Sub1-22 m/z = 408.07(C₂₇H₁₇ClS = 408.94) Sub1-23 m/z =442.11(C₃₁H₁₉ClO = 442.94) Sub1-24 m/z = 508.11(C₃₅H₂₁ClS = 509.06)Sub1-25 m/z = 574.15(C₄₀H₂₇ClS = 575.17) Sub1-26 m/z = 442.11(C₃₁H₁₉ClO= 442.94) Sub1-27 m/z = 442.11(C₃₁H₁₉ClO = 442.94) Sub1-28 m/z =532.12(C₃₇H₂₁ClO₂ = 533.02) Sub1-29 m/z = 443.11(C₃₀H₁₈ClNO = 443.93)Sub1-30 m/z = 416.10(C₂₉H₁₇ClO = 416.90) Sub1-31 m/z =699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-32 m/z = 699.20(C₄₉H₃₀ClNO₂ = 700.23)Sub1-33 m/z = 825.24(C₅₉H₃₆ClNO₂ = 826.39) Sub1-34 m/z =941.31(C₆₈H₄₄ClNO₂ = 942.56) Sub1-35 m/z = 623.17(C₄₃H₂₆ClNO₂ = 624.14)Sub1-36 m/z = 825.24(C₅₉H₃₆ClNO₂ = 826.39) Sub1-37 m/z =699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-38 m/z = 715.17(C₄₉H₃₀ClNOS = 716.3)Sub1-39 m/z = 805.18(C₅₅H₃₂ClNO₂S = 806.38) Sub1-40 m/z =749.21(C₃₃H₃₂ClNO₂ = 750.29) Sub1-41 m/z = 892.29(C₆₃H₄₁ClN₂O₂ = 893.48)Sub1-42 m/z = 623.17(C₄₃H₂₆ClNO₂ = 624.14) Sub1-43 m/z =841.27(C₆₀H₄₀ClNO₂ = 842.44) Sub1-44 m/z = 805.18(C₅₅H₃₂ClNO₂S = 806.38)Sub1-45 m/z = 775.23(C₅₅H₃₄ClNO₂ = 776.33) Sub1-46 m/z =815.26(C₃₈H₃₈ClNO₂ = 816.40) Sub1-47 m/z = 623.17(C₄₃H₂₆ClNO₂ = 624.14)Sub1-48 m/z = 699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-49 m/z =936.22(C₆₃H₃₇ClN₂O₃S = 937.51) Sub1-50 m/z = 855.20(C₃₉H₃₄ClNO₂S =856.44) Sub1-51 m/z = 699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-52 m/z =699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-53 m/z = 897.25(C₆₂H₄₀ClNO₂S = 898.52)Sub1-54 m/z = 957.28(C₆₈H₄₄ClNOS = 958.62) Sub1-55 m/z =739.19(C₅₁H₃₀ClNO₃ = 740.26) Sub1-56 m/z = 917.25(C₆₅H₄₀ClNOS = 918.55)Sub1-57 m/z = 791.20(C₅₅H₃₄ClNOS = 792.39) Sub1-58 m/z =699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-59 m/z = 897.19(C₆₁H₃₆ClNOS₂ = 898.54)Sub1-60 m/z = 749.21(C₃₃H₃₂ClNO₂ = 750.29) Sub1-61 m/z =805.18(C₅₅H₃₂ClNO₂S = 806.38) Sub1-62 m/z = 755.17(C₅₁H₃₀ClNO₂S =756.32) Sub1-63 m/z = 1088.32(C₇₆H₄₉ClN₂O₂S = 1089.75) Sub1-64 m/z =699.20(C₄₉H₃₀ClNO₂ = 700.23) Sub1-65 m/z = 891.29(C₆₄H₄₂ClNO₂ = 892.50)Sub1-66 m/z = 639.14(C₄₃H₂₆ClNOS = 640.20) Sub1-67 m/z =715.17(C₄₉H₃₀ClNOS = 716.30) Sub1-68 m/z = 715.17(C₄₉H₃₀ClNOS = 716.3)Sub1-69 m/z = 841.22(C₃₉H₃₆ClNOS = 842.45) Sub1-70 m/z =957.28(C₆₈H₄₄ClNOS = 958.62) Sub1-71 m/z = 639.14(C₄₃H₂₆ClNOS = 640.20)Sub1-72 m/z = 917.25(C₆₅H₄₀ClNOS = 918.55) Sub1-73 m/z =841.22(C₃₉H₃₆ClNOS = 842.45) Sub1-74 m/z = 731.15(C₄₉H₃₀ClNS₂ = 732.36)Sub1-75 m/z = 821.16(C₅₅H₃₂ClNOS₂ = 822.44) Sub1-76 m/z =765.19(C₅₃H₃₂ClNOS = 766.36) Sub1-77 m/z = 908.26(C₆₃H₄₁ClN₂OS = 909.54)Sub1-78 m/z = 873.23(C₆₀H₄₀ClNS₂ = 874.56) Sub1-79 m/z =731.15(C₄₉H₃₀ClNS₂ = 732.36) Sub1-80 m/z = 821.16(C₅₅H₃₂ClNOS₂ = 822.44)Sub1-81 m/z = 715.17(C₄₉H₃₀ClNOS = 716.30) Sub1-82 m/z =791.20(C₅₅H₃₄ClNOS = 792.39) Sub1-83 m/z = 639.14(C₄₃H₂₆ClNOS = 640.20)Sub1-84 m/z = 847.21(C₃₈H₃₈ClNS₂ = 848.52) Sub1-85 m/z =936.22(C₆₃H₃₇ClN₂O₃S = 937.51) Sub1-86 m/z = 731.15(C₄₉H₃₀ClNS₂ =732.36) Sub1-87 m/z = 731.15(C₄₉H₃₀ClNS₂ = 732.36) Sub1-88 m/z =855.20(C₃₉H₃₄ClNO₂S = 856.44) Sub1-89 m/z = 715.17(C₄₉H₃₀ClNOS = 716.30)Sub1-90 m/z = 947.26(C₆₆H₄₂ClNO₂S = 948.58) Sub1-91 m/z =755.17(C₅₁H₃₀ClNO₂S = 756.32) Sub1-92 m/z = 1007.30(C₇₂H₄₆ClNOS =1008.68) Sub1-93 m/z = 791.20(C₅₅H₃₄ClNOS = 792.39) Sub1-94 m/z =917.25(C₆₅H₄₀ClNOS = 918.55) Sub1-95 m/z = 956.26(C₆₇H₄₁ClN₂OS = 957.59)Sub1-96 m/z = 972.24(C₆₇H₄₁ClN₂S₂ = 973.65) Sub1-97 m/z =765.19(C₅₃H₃₂ClNOS = 766.36) Sub1-98 m/z = 821.16(C₅₅H₃₂ClNOS₂ = 822.44)Sub1-99 m/z = 771.15(C₅₁H₃₀ClNOS₂ = 772.38) Sub1-100 m/z =1104.30(C₇₆H₄₉ClN₂OS₂ = 1105.81) Sub1-101 m/z = 907.27(C₆₄H₄₂ClNOS =908.56) Sub1-102 m/z = 715.17(C₄₉H₃₀ClNOS = 716.03) Sub1-103 m/z =1032.31(C₇₃H₄₅ClN₂O₃ = 1033.62) Sub1-104 m/z = 1048.29(C₇₃H₄₅ClN₂O₂S =1049.69) Sub1-105 m/z = 1048.29(C₇₃H₄₅ClN₂O₂S = 1049.69) Sub1-106 m/z =1154.28(C₇₉H₄₇ClN₂O₂S₂ = 1155.83) Sub1-107 m/z = 1264.35(C₈₉H₃₃ClN₂O₃S =1265.92) Sub1-108 m/z = 1174.34(C₈₃H₅₁ClN₂O₂S = 1175.84) Sub1-109 m/z =1406.42(C₁₀₀H₆₃ClN₂O₃S = 1408.13) Sub1-110 m/z = 1274.39(C₉₁H₅₅ClN₂O₄ =1275.90) Sub1-111 m/z = 1240.38(C₈₈H₅₇ClN₂O₂S = 1241.95) Sub1-112 m/z =1048.29(C₇₃H₄₅ClN₂O₂S = 1049.69) Sub1-113 m/z = 1174.34(C₈₃H₅₁ClN₂O₂S =1175.84) Sub1-114 m/z = 1190.31(C₈₃H₅₁ClN₂OS₂ = 1191.90) Sub1-115 m/z =1138.30(C₇₉H₄₇ClN₂O₃S = 1139.77) Sub1-116 m/z = 1154.28(C₇₉H₄₇ClN₂O₂S₂ =1155.83) Sub1-117 m/z = 1048.29(C₇₃H₄₅ClN₂O₂S = 1049.69) Sub1-118 m/z =1270.34(C₈₈H₅₅ClN₂O₂S₂ = 1271.99) Sub1-119 m/z = 1188.32(C₈₃H₄₉ClN₂O₃S =1189.83) Sub1-120 m/z = 1214.37(C₈₆H₅₅ClN₂O₂S = 1215.91) Sub1-121 m/z =1141.29(C₇₈H₄₈ClN₃OS₂ = 1142.83) Sub1-122 m/z = 1140.30(C₇₉H₄₉ClN₂OS₂ =1141.84) Sub1-123 m/z = 1141.29(C₇₈H₄₈ClN₃OS₂ = 1142.83) Sub1-124 m/z =1250.37(C₈₉H₅₅ClN₂O₂S = 1251.94) Sub1-125 m/z = 1124.32(C₇₉H₄₉ClN₂O₂S =1125.78) Sub1-126 m/z = 1266.34(C₈₉H₅₅ClN₂OS₂ = 1268.00) Sub1-127 m/z =1229.32(C₈₅H₅₂ClN₃OS₂ = 1230.94) Sub1-128 m/z = 1229.32(C₈₅H₅₂ClN₃OS₂ =1230.94) Sub1-129 m/z = 1048.29(C₇₃H₄₅ClN₂O₂S = 1049.69) Sub1-130 m/z =1114.28(C₇₇H₄₇ClN₂OS₂ = 1115.81) Sub1-131 m/z = 1170.25(C₇₉H₄₇ClN₂OS₃ =1171.89) Sub1-132 m/z = 1204.29(C₈₃H₄₉ClN₂O₂S₂ = 1205.89) Sub1-133 m/z =1477.44(C₁₀₃H₆₈ClN₃O₂S₂ = 1479.27) Sub1-134 m/z = 1154.28(C₇₉H₄₇ClN₂O₂S₂= 1155.83) Sub1-135 m/z = 1471.49(C₁₀₅H₇₀ClN₃O₂S = 1473.24) Sub1-136 m/z= 1064.27(C₇₃H₄₃ClN₂OS₂ = 1065.75) Sub1-137 m/z = 1256.36(C₈₈H₅₇ClN₂OS₂= 1258.01) Sub1-138 m/z = 1240.38(C₈₈H₅₇ClN₂O₂S = 1241.95) Sub1-139 m/z= 1140.30(C₇₉H₄₉ClN₂OS₂ = 1141.84) Sub1-140 m/z = 1140.30(C₇₉H₄₉ClN₂OS₂= 1141.84) Sub1-141 m/z = 1124.32(C₇₉H₄₉ClN₂O₂S = 1125.78) Sub1-142 m/z= 1170.25(C₇₉H₄₇ClN₂OS₃ = 1171.89) Sub1-143 m/z = 1280.32(C₈₉H₅₃ClN₂O₂S₂= 1281.99) Sub1-144 m/z = 1190.31(C₈₃H₅₁ClN₂OS₂ = 1191.90) Sub1-145 m/z= 1422.40(C₁₀₀H₆₃ClN₂O₂S₂ = 1424.19) Sub1-146 m/z =1290.36(C₉₁H₅₅ClN₂O₃S = 1291.96) Sub1-147 m/z = 1256.36(C₈₈H₅₇ClN₂OS₂ =1258.01) Sub1-148 m/z = 1256.31(C₈₇H₅₃ClN₂S₃ = 1258.03) Sub1-149 m/z =1130.26(C₇₇H₄₇ClN₂S₃ = 1131.87) Sub1-150 m/z = 1206.29(C₈₃H₅₁ClN₂S₃ =1207.97) Sub1-151 m/z = 1236.39(C₈₃H₆₂Cl₂N₂O₃S = 1238.38) Sub1-152 m/z =1493.57(C₁₀₃H₈₄ClN₃O₂S₂ = 1495.39) Sub1-153 m/z =1599.56(C₁₀₉H₈₆ClN₃O₂S₃ = 1601.54) Sub1-154 m/z = 1214.24(C₈₁H₄₈Cl₂N₂S₃= 1216.37) Sub1-155 m/z = 1082.25(C₇₃H₄₄Cl₂N₂O₂S = 1084.13) Sub1-156 m/z= 508.11(C₃₅H₂₁ClS = 509.06) Sub1-157 m/z = 442.11(C₃₁H₁₉ClO = 442.94)Sub1-158 m/z = 1252.36(C₈₃H₆₂Cl₂N₂O₂S₂ = 1254.44) Sub1-159 m/z =1509.55(C₁₀₃H₈₄ClN₃OS₃ = 1511.46) Sub1-160 m/z = 1615.53(C₁₀₉H₈₆ClN₃OS₄= 1617.60) Sub1-161 m/z = 391.08(C₂₆H₁₄ClNO = 391.85) Sub1-162 m/z =459.08(C₃₀H₁₈ClNS = 459.99) Sub1-163 m/z = 442.11(C₃₁H₁₉ClO = 442.94)Sub1-164 m/z = 442.11(C₃₁H₁₉ClO = 442.94) Sub1-165 m/z =442.11(C₃₁H₁₉ClO = 442.94) Sub1-166 m/z = 458.09(C₃₁H₁₉ClS = 459.00)Sub1-167 m/z = 458.09(C₃₁H₁₉ClS = 459.00) Sub1-168 m/z =458.09(C₃₁H₁₉ClS = 459.00) Sub1-169 m/z = 391.08(C₂₆H₁₄ClNO = 391.85)Sub1-170 m/z = 408.07(C₂₇H₁₇ClS = 408.94) Sub1-171 m/z =416.10(C₂₉H₁₇ClO = 416.90) Sub1-172 m/z = 460.08(C₂₉H₁₇ClN₂S = 460.98)

II. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction route ofScheme 3 below, but is not limited thereto. Sub 3 and Sub 4 are alsoincluded in Sub 2.

In Reaction Scheme 3,

Y, Ar¹′, Ar²′, R¹′, L¹′, e′ and f′ are the same as defined above, Hal¹′is Br or Cl.

Synthesis examples of specific compounds belonging to Sub 2 are asfollows.

1. Synthesis Example of Sub 2-8

(1) Synthesis Example of Sub 2-8-a

4-bromo-2-chlorophenol (15 g, 73.5 mmole) was dissolved in a roundbottom flask with DMF (400 mL) and iodobenzene (16.8 g, 80.9 mmol),K₂CO₃ (20.3 g 147.1 mmol), Cu (2.3 g, 36.8 mmol), Dibenzo-18-crown-6(1.6 g, 4.4 mmole) were added and stirred at 120° C. When the reactionwas completed, the solvent was removed, extracted with CH₂Cl₂ and water,the organic layer was dried over MgSO₄, concentrated, and the resultingcompound was silicagel column to obtain 16.5 g (yield 79%) of theproduct.

(2) Synthesis Example of Sub 2-8-b

Acetic acid (400 mL) was added to 4-bromo-2-chloro-1-phenoxybenzene (16g, 56.4 mmol)⁰∥ Pd(OAc)₂ (0.63 g, 2.8 mol), K₂CO₃ (7.8 g, 56.4 mol) andstirred at 120° C. for 48 hours. When the reaction was completed, thesolvent was removed, extracted with Ethyl Acetate and water, the organiclayer was dried over MgSO₄, concentrated, and the resulting compound wassilicagel column to obtain 6.7 g (yield 42%) of the product.

(3) Synthesis Example of Sub 2-8-c

Sub 2-8-b (6.7 g, 23.8 mmol) obtained in the above synthesis,phenylboronic acid (2.9 g, 23.8 mmol) was added, dissolved in THF (100mL), and Pd(PPh₃)₄ (1.4 g, 1.2 mmol) and K₂CO₃ (19.9 g, 71.4 mmol) wereadded, respectively, and then refluxed for 24 hours. When the reactionwas completed, the solvent was removed, extracted with CH₂Cl₂ and water,the organic layer was dried over MgSO₄, concentrated, and the resultingcompound was silicagel column to obtain 4.98 g (yield 75%) of theproduct.

(4) Synthesis Example of Sub 2-8

After dissolving Sub 2-8-c (4.98 g, 17.9 mmol) obtained in the abovesynthesis with Toluene (100 ml) in a round bottom flask, Aniline (1.83g, 19.7 mmol), Pd₂(dba)₃ (0.49 g, 0.54 mmol), P(t-Bu)₃ (50 wt % Sol.)(0.43 mL, 1.07 mmol), NaOt-Bu (5.2 g, 53.6 mmol) were added and stirredat 80° C. When the reaction was completed, the solvent was removed,extracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄,concentrated, and the resulting compound was silicagel column to obtain4.8 g (yield 80%) of the product.

2. Synthesis Example of Sub 2-43

(1) Synthesis Example of Sub 2-43-a

(2-(methylthio)phenyl)boronic acid (30 g, 137.6 mmol) was dissolved in around bottom flask with THF (300 mL) and 4-bromo-2-chloroiodobenzene(43.7 g, 137.6 mmol), Pd(PPh₃)₄ (4.8 g, 4.1 mmol), K₂CO₃ (57 g, 412.7mmol), and water (100 mL) were added and stirred at 80° C. When thereaction was completed, the solvent was removed, extracted with CH₂Cl₂and water, the organic layer was dried over MgSO₄, concentrated, and theresulting compound was silicagel column to obtain 37.5 g (yield 75%) ofthe product.

(2) Synthesis Example of Sub 2-43-a′

Sub 2-43-a (37 g, 101.7 mmol) obtained in the above synthesis wasdissolved in AcOH (300 mL) in a round bottom flask, H₂O₂ (8.7 mL, 101.7mmol) was added and stirred at room temperature. When the reaction wascompleted, the solvent was removed, neutralized with 1M NaOH, extractedwith Ethyl acetate, and recrystallized to obtain 35.5 g (92% yield) ofthe product.

(3) Synthesis Example of Sub 2-43-b

Sub 2-43-a′ (35 g, 92.2 mmol) obtained in the above synthesis was addedto 300 g of Trifluloromethanesulfonic acid and stirred at 65° C. Whenthe reaction was completed, pyridine was added and refluxed for 30minutes, and the resulting compound was recrystallized in a silicagelcolumn to obtain 26 g (yield 81%) of the product.

(4) Synthesis Example of Sub 2-43-c

Sub 2-43-b (26 g, 74.8 mmol) obtained in the above synthesis,phenylboronic acid (9.12 g, 74.8 mmol), Pd(PPh₃)₄ (4.32 g, 3.7 mmol),K₂CO₃ (62.54 g, 224.4 mmol) was added to THF (180 mL), and by using thesynthesis method of Sub 2-8-c, the product 20.1 g (78% yield) wasobtained.

(5) Synthesis Example of Sub 2-43

Sub 2-43-c (20.1 g, 58.3 mmol) obtained in the above synthesis wasdissolved in a round bottom flask with Toluene (400 ml), and Aniline (6g, 64.1 mmol), Pd₂(dba)₃ (1.6 g, 1.75 mmol), P(t-Bu)₃ (50 wt % Sol.)(1.42 mL, 3.5 mmol), NaOt-Bu (16.8 g, 174.85 mmol) were added, andproduct 23.4 g (yield 79%) was obtained using the synthesis method ofSub 2-8.

Meanwhile, the compound belonging to Sub 2 may be the followingcompound, but is not limited thereto. Sub 3 and Sub 4 are also compoundsbelonging to Sub 2, and Table 2 below shows the FD-MS values of thecompounds belonging to Sub 2.

TABLE 2 compound FD-MS compound FD-MS Sub2-1 m/z = 335.13(C₂₄H₁₇NO =335.41) Sub2-2 m/z = 427.19(C₃₁H₂₅NO = 427.55) Sub2-3 m/z =561.21(C₄₂H₂₇NO = 561.68) Sub2-4 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub2-5m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub2-6 m/z = 435.16(C₂₄H₁₇NO = 435.53)Sub2-7 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub2-8 m/z = 335.13(C₃₂H₂₁NO =335.41) Sub2-9 m/z = 527.22(C₃₉H₂₉NO = 527.67) Sub2-10 m/z =511.19(C₃₈H₂₅NO = 511.62) Sub2-11 m/z = 487.19(C₃₅H₂₅NO = 487.60)Sub2-12 m/z = 537.21(C₄₀H₂₇NO = 537.66) Sub2-13 m/z = 435.16(C₃₂H₂₁NO =435.53) Sub2-14 m/z = 336.13(C₂₃H₁₅N₂O = 336.39) Sub2-15 m/z =452.15(C₃₁H₂₀N₂O₂ = 452.51) Sub2-16 m/z = 500.19(C₃₅H₂₄N₂O = 500.60)Sub2-17 m/z = 465.20(C₃₄H₁₉D₄NO = 465.59) Sub2-18 m/z =482.11(C₃₁H₁₈N₂O₂S = 482.56) Sub2-19 m/z = 567.17(C₄₀H₂₅NOS = 567.71)Sub2-20 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub2-21 m/z = 475.14(C₃₄H₂₁NS =475.61) Sub2-22 m/z = 477.16(C₃₄H₂₃NS = 477.63) Sub2-23 m/z =577.19(C₄₂H₂₇NS = 577.75) Sub2-24 m/z = 477.16(C₃₄H₂₃NS = 477.63)Sub2-25 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub2-26 m/z = 427.14(C₃₀H₂₁NS =427.57) Sub2-27 m/z = 441.12(C₃₀H₁₉NOS = 441.55) Sub2-28 m/z =427.14(C₃₀H₂₁NS = 427.57) Sub2-29 m/z = 457.10(C₃₀H₁₉NS₂ = 457.61)Sub2-30 m/z = 527.17(C₃₈H₂₅NS = 527.69) Sub2-31 m/z = 517.15(C₃₆H₂₃NOS =517.65) Sub2-32 m/z = 352.10(C₂₃H₁₆N₂S = 352.46) Sub2-33 m/z =451.14(C₃₂H₂₁NS = 451.59) Sub2-34 m/z = 553.19(C₄₀H₂₇NS = 553.72)Sub2-35 m/z = 503.17(C₃₅H₂₅NS = 503.66) Sub2-36 m/z = 451.14(C₃₂H₂₁NS =451.59) Sub2-37 m/z = 592.20(C₄₂H₂₈N₂S = 592.76) Sub2-38 m/z =583.14(C₄₀H₂₅NS₂ = 583.77) Sub2-39 m/z = 385.15(C₂₈H₁₉NO = 385.47)Sub2-40 m/z = 352.10(C₂₃H₁₆N₂S = 352.46) Sub2-41 m/z = 401.12(C₂₈H₁₉NS =401.53) Sub2-42 m/z = 477.16(C₃₄H₂₃NS = 477.63) Sub2-43 m/z =507.11(C₃₄H₂₁NS₂ = 507.67) Sub2-44 m/z = 553.19(C₄₀H₂₇NS = 553.72)Sub2-45 m/z = 527.17(C₃₈H₂₅NS = 527.69) Sub2-46 m/z = 517.15(C₃₆H₂₃NOS =517.65) Sub2-47 m/z = 498.09(C₃₁H₁₈N₂OS₂ = 498.62) Sub2-48 m/z =427.14(C₃₀H₂₁NS = 427.57) Sub2-49 m/z = 468.13(C₃₁H₂₀N₂OS = 468.57)Sub2-50 m/z = 385.15(C₂₈H₁₉NO = 385.47) Sub2-51 m/z = 441.12(C₃₀H₁₉NOS =441.55) Sub2-52 m/z = 367.14(C₂₅H₂₁NS = 367.51) Sub2-53 m/z =577.24(C₄₃H₃₁NO = 577.73) Sub2-54 m/z = 351.16(C₂₅H₂₁NO = 351.45)Sub2-55 m/z = 435.16(C₃₂H₂₁NO = 435.53) Sub2-56 m/z = 451.19(C₃₃H₂₅NO =451.57) Sub2-57 m/z = 427.19(C₃₁H₂₅NO = 427.55) Sub2-58 m/z =441.12(C₃₀H₁₉NOS = 441.55) Sub2-59 m/z = 477.21(C₃₅H₂₇NO = 477.61)Sub2-60 m/z = 528.22(C₃₈H₂₈N₂O = 528.66) Sub2-61 m/z = 375.13(C₂₆H₁₇NO₂= 375.43) Sub2-62 m/z = 609.25(C₄₄H₃₅NS = 609.83) Sub2-63 m/z =533.18(C₃₇H₂₇NOS = 533.69) Sub2-64 m/z = 507.17(C₃₅H₂₅NOS = 507.65)Sub2-65 m/z = 572.16(C₃₈H₂₄N₂O₂S = 572.68) Sub2-66 m/z =391.10(C₂₅H₁₇NOS = 391.49) Sub2-67 m/z = 724.25(C₅₁H₃₆N₂OS = 724.92)Sub2-68 m/z = 527.22(C₃₉H₂₉NO = 527.67) Sub2-69 m/z = 441.12(C₃₀H₁₉NOS =441.55) Sub2-70 m/z = 493.19(C₃₅H₂₇NS = 493.67) Sub2-71 m/z =467.17(C₃₃H₂₅NS = 467.63) Sub2-72 m/z = 556.18(C₃₈H₂₄N₂O₃ = 556.62)Sub2-73 m/z = 475.16(C₃₄H₂₁NO₂ = 475.55) Sub2-74 m/z = 567.22(C₄₁H₂₉NO₂= 567.69) Sub2-75 m/z = 627.26(C₄₇H₃₃NO = 627.79) Sub2-76 m/z =527.22(C₃₉H₂₉NO = 527.67) Sub2-77 m/z = 335.13(C₂₄H₁₇NO = 335.41)Sub2-78 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub2-79 m/z = 501.17(C₃₆H₂₃NO₂ =501.59) Sub2-80 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub2-81 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub2-82 m/z = 516.17(C₃₅H₂₄N₂S = 516.66)Sub2-83 m/z = 708.31(C₅₂H₄₀N₂O = 708.91) Sub2-84 m/z = 401.12(C₂₈H₁₉NS =401.53) Sub2-85 m/z = 401.12(C₂₈H₁₉NS = 401.53) Sub2-86 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub2-87 m/z = 518.18(C₃₆H₂₆N₂S = 518.68)Sub2-88 m/z = 427.14(C₃₀H₂₁NS = 427.57) Sub2-89 m/z = 461.18(C₃₄H₂₃NO =461.56) Sub2-90 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub2-91 m/z =335.13(C₂₄H₁₇NO = 335.41) Sub2-92 m/z = 561.21(C₄₂H₂₇NO = 561.68)Sub2-93 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub2-94 m/z = 353.12(C₂₄H₁₆FNO =353.40) Sub2-95 m/z = 391.19(C₂₈H₂₅NO = 391.51) Sub2-96 m/z =259.10(C₁₈H₁₃NO = 259.31) Sub2-97 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub3-1m/z = 375.16(C₂₇H₂₁NO = 375.47) Sub3-2 m/z = 375.16(C₂₇H₂₁NO = 375.47)Sub3-3 m/z = 375.16(C₂₇H₂₁NO = 375.47) Sub3-4 m/z = 391.14(C₂₇H₂₁NS =391.53) Sub3-5 m/z = 499.19(C₃₇H₂₅NO = 499.61) Sub3-6 m/z =499.19(C₃₇H₂₅NO = 499.61) Sub3-7 m/z = 499.19(C₃₇H₂₅NO = 499.61) Sub3-8m/z = 499.19(C₃₇H₂₅NO = 499.61) Sub3-9 m/z = 515.17(C₃₇H₂₅NS = 515.67)Sub3-10 m/z = 497.18(C₃₇H₂₃NO = 497.60) Sub3-11 m/z = 513.16(C₃₇H₂₃NS =513.66) Sub3-12 m/z = 451.19(C₃₃H₂₅NO = 451.57) Sub3-13 m/z =467.17(C₃₃H₂₅NS = 467.63) Sub3-14 m/z = 451.19(C₃₃H₂₅NO = 451.57)Sub3-15 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub3-16 m/z = 451.19(C₃₃H₂₅NO =451.57) Sub3-17 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub3-18 m/z =451.19(C₃₃H₂₅NO = 451.57) Sub3-19 m/z = 451.19(C₃₃H₂₅NO = 451.57)Sub3-20 m/z = 451.19(C₃₃H₂₅NO = 451.57) Sub3-21 m/z = 451.19(C₃₃H₂₅NO =451.57) Sub3-22 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub3-23 m/z =467.17(C₃₃H₂₅NS = 467.63) Sub3-24 m/z = 467.17(C₃₃H₂₅NS = 467.63)Sub3-25 m/z = 501.21(C₃₇H₂₇NO = 501.63) Sub3-26 m/z = 517.19(C₃₇H₂₇NS =517.69) Sub3-27 m/z = 501.21(C₃₇H₂₇NO = 501.63) Sub3-28 m/z =517.19(C₃₇H₂₇NS = 517.69) Sub3-29 m/z = 501.21(C₃₇H₂₇NO = 501.63)Sub3-30 m/z = 517.19(C₃₇H₂₇NS = 517.69) Sub3-31 m/z = 452.19(C₃₂H₂₄N₂O =452.56) Sub3-32 m/z = 583.23(C₄₂H₃₃NS = 583.79) Sub3-33 m/z =525.21(C₃₉H₂₇NO = 525.65) Sub3-34 m/z = 519.20(C₃₇H₂₁D₄NS = 519.70)Sub3-35 m/z = 527.22(C₃₉H₂₉NO = 527.67) Sub3-36 m/z = 543.20(C₃₉H₂₉NS =543.73) Sub3-37 m/z = 527.22(C₃₉H₂₉NO = 527.67) Sub3-38 m/z =543.20(C₃₉H₂₉NS = 543.73) Sub3-39 m/z = 543.20(C₃₉H₂₉NS = 543.73)Sub3-40 m/z = 527.22(C₃₉H₂₉NO = 527.67) Sub3-41 m/z = 527.22(C₃₉H₂₉NO =527.67) Sub3-42 m/z = 527.22(C₃₉H₂₉NO = 527.67) Sub3-43 m/z =543.20(C₃₉H₂₉NS = 543.73) Sub3-44 m/z = 543.20(C₃₉H₂₉NS = 543.73)Sub3-45 m/z = 452.19(C₃₂H₂₄N₂O = 452.56) Sub3-46 m/z = 441.16(C₃₁H₂₃NS =441.59) Sub3-47 m/z = 441.16(C₃₁H₂₃NS = 441.59) Sub3-48 m/z =425.18(C₃₁H₂₃NO = 425.53) Sub3-49 m/z = 425.18(C₃₁H₂₃NO = 425.53)Sub3-50 m/z = 467.17(C₃₃H₂₅NS = 467.63) Sub3-51 m/z = 577.24(C₄₃H₃₁NO =577.73) Sub3-52 m/z = 573.21(C₄₃H₂₇NO = 573.70) Sub3-53 m/z =497.18(C₃₇H₂₃NO = 497.60) Sub3-54 m/z = 497.18(C₃₇H₂₃NO = 497.60)Sub3-55 m/z = 513.16(C₃₇H₂₃NS = 513.66) Sub3-56 m/z = 441.16(C₃₁H₂₃NS =441.59) Sub3-57 m/z = 549.21(C₄₁H₂₇NO = 549.67) Sub4-1 m/z =513.17(C₃₇H₂₃NO₂ = 513.60) Sub4-2 m/z = 513.17(C₃₇H₂₃NO₂ = 513.60)Sub4-3 m/z = 513.17(C₃₇H₂₃NO₂ = 513.60) Sub4-4 m/z = 513.17(C₃₇H₂₃NO₂ =513.60) Sub4-5 m/z = 579.17(C₄₁H₂₅NOS = 579.72) Sub4-6 m/z =531.16(C₃₇H₂₂FNO₂ = 531.59) Sub4-7 m/z = 563.19(C₄₁H₂₅NO₂ = 563.66)Sub4-8 m/z = 665.24(C₄₉H₃₁NO₂ = 665.79) Sub4-9 m/z = 529.15(C₃₇H₂₃NOS =529.66) Sub4-10 m/z = 529.15(C₃₇H₂₃NOS = 529.66) Sub4-11 m/z =529.15(C₃₇H₂₃NOS = 529.66) Sub4-12 m/z = 529.15(C₃₇H₂₃NOS = 529.66)Sub4-13 m/z = 529.15(C₃₇H₂₃NOS = 529.66) Sub4-14 m/z = 529.15(C₃₇H₂₃NOS= 529.66) Sub4-15 m/z = 529.15(C₃₇H₂₃NOS = 529.66) Sub4-16 m/z =529.15(C₃₇H₂₃NOS = 529.66) Sub4-17 m/z = 545.13(C₃₇H₂₃NS₂ = 545.72)Sub4-18 m/z = 589.20(C₄₃H₂₇NO₂ = 589.69) Sub4-19 m/z = 605.18(C₄₃H₂₇NOS= 605.76) Sub4-20 m/z = 605.18(C₄₃H₂₇NOS = 605.76) Sub4-21 m/z =621.16(C₄₃H₂₇NS₂ = 621.82) Sub4-22 m/z = 655.20(C₄₇H₂₉NOS = 655.82)Sub4-23 m/z = 671.17(C₄₇H₂₉NS₂ = 671.88) Sub4-24 m/z = 606.18(C₄₂H₂₅N₂OS= 606.74) Sub4-25 m/z = 622.15(C₄₂H₂₅N₂S₂ = 622.80) Sub4-26 m/z =589.20(C₄₃H₂₇NO₂ = 589.69) Sub4-27 m/z = 605.18(C₄₃H₂₇NOS = 605.76)Sub4-28 m/z = 589.20(C₄₃H₂₇NO₂ = 589.69) Sub4-29 m/z = 605.18(C₄₃H₂₇NOS= 605.76) Sub4-30 m/z = 605.18(C₄₃H₂₇NOS = 605.76) Sub4-31 m/z =621.16(C₄₃H₂₇NS₂ = 621.82) Sub4-32 m/z = 563.19(C₄₁H₂₅NO₂ = 563.66)Sub4-33 m/z = 595.14(C₄₁H₂₅NS₂ = 595.78) Sub4-34 m/z = 579.17(C₄₁H₂₅NOS= 579.72) Sub4-35 m/z = 605.18(C₄₃H₂₇NOS = 605.76) Sub4-36 m/z =671.17(C₄₇H₂₉NS₂ = 671.88) Sub4-37 m/z = 665.24(C₄₉H₃₁NO₂ = 665.79)Sub4-38 m/z = 549.15(C₃₇H₁₉D₄NS₂ = 549.74) Sub4-39 m/z =665.24(C₄₉H₃₁NO₂ = 665.79) Sub4-40 m/z = 589.20(C₄₃H₂₇NO₂ = 589.69)Sub4-41 m/z = 671.17(C₄₇H₂₉NS₂ = 671.88) Sub4-42 m/z = 595.14(C₄₁H₂₅NS₂= 595.78) Sub4-43 m/z = 595.14(C₄₁H₂₅NS₂ = 595.78) Sub4-44 m/z =563.19(C₄₁H₂₅NO₂ = 563.66)

III. Synthesis of Final Product 1. Synthesis Example of P-1

Sub1-1 (20 g, 54.5 mmol) was dissolved in a round bottom flask withToluene (400 mL) and Sub2-1 (18.3 g, 54.5 mmol), Pd₂(dba)₃ (1.5 g, 1.64mmol), P(t-Bu)₃ (50 wt % Sol.) (1.3 mL, 3.3 mmol), NaOt-Bu (15.7 g,163.6 mmol) were added and stirred at 80° C. When the reaction wascompleted, the solvent was removed, extracted with CH₂Cl₂ and water, theorganic layer was dried over MgSO₄, concentrated, and the resultingcompound was purified by silicagel column and sublimation to obtain 29.8g (82% yield) of the product.

2. Synthesis Example of P-73

Sub1-27 (17 g, 38.4 mmol) and Sub2-88 (16.4 g, 38.4 mmol), Pd₂(dba)₃(1.05 g, 1.15 mmol), NaOt-Bu (11.06 g, 115.14 mmol), Anhydrous Toluene(340 mL), P(t-Bu)₃ (50 wt % Sol.) (0.93 mL, 2.3 mmol) were obtained 20.4g (80% yield) of P-73 using the synthesis method of P-1.

3. Synthesis Example of P-113

Sub1-87 (12 g, 16.4 mmol) and Sub2-73 (7.8 g, 16.4 mmol), Pd₂(dba)₃(0.45 g, 0.5 mmol), NaOt-Bu (4.7 g, 49.2 mmol), anhydroups Toluene (240mL), P(t-Bu)₃ (50 wt % Sol.) (0.2 mL, 0.98 mmol) were obtained 14.2 g(74% yield) of P-113 using the synthesis method of P-1.

4. Synthesis Example of P-121

Sub1-105 (12 g, 11.4 mmol) and Sub2-77 (3.8 g, 11.4 mmol), Pd₂(dba)₃(0.3 g, 0.34 mmol), NaOt-Bu (3.3 g, 34.3 mmol), anhydrous Toluene (240mL), P(t-Bu)₃ (50 wt % Sol.) (0.3 mL, 0.7 mmol) were obtained 11.7 g(76% yield) of P-121 using the synthesis method of P-1.

5. Synthesis Example of P-139

Sub1-160 (9 g, 7.8 mmol) and Sub2-69 (3.5 g, 7.8 mmol), Pd₂(dba)₃ (0.2g, 0.23 mmol), NaOt-Bu (2.3 g, 23.5 mmol), anhydrous Toluene (180 mL),P(t-Bu)₃ (50 wt % Sol.) (0.2 mL, 0.5 mmol) were obtained 10.9 g (73%yield) of P-139 using the synthesis method of P-1.

6. Synthesis Example of P 1-2

Sub1-1 (15 g, 40.9 mmol) and Sub2-95 (16.0 g, 40.9 mmol), Pd₂(dba)₃(1.12 g, 1.2 mmol), NaOt-Bu (11.8 g, 122.7 mmol), anhydrous Toluene (300mL), P(t-Bu)₃ (50 wt % Sol.) (1.00 mL, 2.5 mmol) were obtained 24.2 g(84% yield) of P1-2 using the synthesis method of P-1.

7. Synthesis Example of P 1-13

Sub1-1 (10.2 g, 27.8 mmol) and Sub3-12 (12.6 g, 27.8 mmol), Pd₂(dba)₃(0.8 g, 0.76 mmol), NaOt-Bu (8.0 g, 83.4 mmol), anhydrous Toluene (210mL), P(t-Bu)₃ (50 wt % Sol.) (0.7 mL, 1.7 mmol) were obtained 17.6 g(81% yield) of P1-13 using the synthesis method of P-1.

8. Synthesis Example of P 2-3

Sub1-1 (9.5 g, 25.9 mmol) and Sub4-3 (13.3 g, 25.9 mmol), Pd₂(dba)₃ (0.7g, 0.8 mmol), NaOt-Bu (7.5 g, 77.7 mmol), anhydrous Toluene (200 mL),P(t-Bu)₃ (50 wt % Sol.) (0.6 mL, 0.8 mmol) were obtained 18.1 g (83%yield) of P2-3 using the synthesis method of P-1.

The FD-MS values of compounds P-1 to P-139, P1-1 to P1-86, and P2-1 toP2-55 of the present invention prepared according to the synthesisexample as described above are shown in Table 3 below.

TABLE 3 Compound FD-MS compound FD-MS P-1 m/z = 665.24(C₄₉H₃₁NO₂ =665.79) P-2 m/z = 791.28(C₅₉H₃₇NO₂ = 791.95) P-3 m/z = 891.31(C₅₇H₄₁NO₂= 892.07) P-4 m/z = 741.27(C₅₅H₃₅NO₂ = 741.89) P-5 m/z =791.28(C₅₉H₃₇NO₂ = 791.95) P-6 m/z = 665.24(C₄₉H₃₁NO₂ = 665.79) P-7 m/z= 665.24(C₄₉H₃₁NO₂ = 665.79) P-8 m/z = 665.24(C₄₉H₃₁NO₂ = 665.79) P-9m/z = 665.24(C₄₉H₃₁NO₂ = 665.79) P-10 m/z = 857.33(C₆₄H₄₃NO₂ = 858.05)P-11 m/z = 841.30(C₅₃H₃₉NO₂ = 842.01) P-12 m/z = 817.30(C₅₁H₃₉NO₂ =817.99) P-13 m/z = 867.31(C₅₅H₄₁NO₂ = 868.05) P-14 m/z =833.30(C₅₀H₃₉N₃O₂ = 833.99) P-15 m/z = 666.23(C₄₈H₃₀N₂O₂ = 666.78) P-16m/z = 782.26(C₅₅H₃₄N₂O₃ = 782.90) P-17 m/z = 830.29(C₅₁H₃₈N₂O₂ = 830.99)P-18 m/z = 795.31(C₅₉H₃₃D₄NO₂ = 795.97) P-19 m/z = 812.21(C₅₆H₃₂N₂O₃S =812.94) P-20 m/z = 897.27(C₅₅H₃₉NO₂S = 898.09) P-21 m/z =681.21(C₄₉H₃₁NOS = 681.85) P-22 m/z = 807.26(C₅₉H₃₇NOS = 808.01) P-23m/z = 907.29(C₅₇H₄₁NOS = 908.13) P-24 m/z = 807.26(C₅₉H₃₇NOS = 808.01)P-25 m/z = 805.24(C₅₉H₃₅NOS = 806.00) P-26 m/z = 797.28(C₅₈H₃₉NOS =798.02) P-27 m/z = 757.24(C₅₅H₃₅NOS = 757.95) P-28 m/z =771.22(C₅₅H₃₃NO₂S = 771.93) P-29 m/z = 757.24(C₅₅H₃₅NOS = 757.95) P-30m/z = 787.20(C₅₅H₃₃NOS₂ = 788.00) P-31 m/z = 857.28(C₆₃H₃₉NOS = 858.07)P-32 m/z = 833.28(C₆₁H₃₉NOS = 834.05) P-33 m/z = 883.29(C₅₅H₄₁NOS =884.11) P-34 m/z = 781.24(C₅₇H₃₅NOS = 781.97) P-35 m/z =682.21(C₄₈H₃₀N₂OS = 682.84) P-36 m/z = 681.21(C₄₉H₃₁NOS = 681.85) P-37m/z = 807.26(C₅₉H₃₇NOS = 808.01) P-38 m/z = 907.29(C₅₇H₄₁NOS = 908.13)P-39 m/z = 807.26(C₅₉H₃₇NOS = 808.01) P-40 m/z = 807.26(C₅₉H₃₇NOS =808.01) P-41 m/z = 681.21(C₄₉H₃₁NOS = 681.85) P-42 m/z =681.21(C₄₉H₃₁NOS = 681.85) P-43 m/z = 681.21(C₄₉H₃₁NOS = 681.85) P-44m/z = 681.21(C₄₉H₃₁NOS = 681.85) P-45 m/z = 873.31(C₅₄H₄₃NOS = 874.11)P-46 m/z = 857.28(C₆₃H₃₉NOS = 858.07) P-47 m/z = 833.28(C₆₁H₃₉NOS =834.05) P-48 m/z = 883.29(C₅₅H₄₁NOS = 884.11) P-49 m/z =781.24(C₅₇H₃₅NOS = 781.97) P-50 m/z = 682.21(C₄₈H₃₀N₂OS = 682.84) P-51m/z = 798.23(C₅₅H₃₄N₂O₂S = 798.96) P-52 m/z = 846.27(C₅₁H₃₈N₂OS =847.05) P-53 m/z = 811.28(C₅₉H₃₃D₄NOS = 812.04) P-54 m/z =828.19(C₅₅H₃₂N₂O₂S₂ = 829.00) P-55 m/z = 863.23(C₅₁H₃₇NOS₂ = 864.09)P-56 m/z = 823.24(C₅₉H₃₇NS₂ = 824.07) P-57 m/z = 863.23(C₅₁H₃₇NOS₂ =864.09) P-58 m/z = 929.22(C₅₅H₃₉NS₃ = 930.21) P-59 m/z =938.28(C₅₇H₄₂N₂S₂ = 939.21) P-60 m/z = 797.22(C₅₇H₃₅NS₂ = 798.03) P-61m/z = 813.25(C₅₈H₃₉NS₂ = 814.08) P-62 m/z = 773.22(C₅₅H₃₅NS₂ = 774.01)P-63 m/z = 747.21(C₅₃H₃₃NS₂ = 747.97) P-64 m/z = 823.24(C₅₉H₃₇NS₂ =824.07) P-65 m/z = 853.19(C₅₉H₃₅NS₃ = 854.12) P-66 m/z =923.27(C₅₇H₄₁NS₂ = 924.19) P-67 m/z = 949.28(C₆₉H₄₃NS₂ = 950.23) P-68m/z = 781.24(C₅₇H₃₅NOS = 781.97) P-69 m/z = 847.24(C₅₁H₃₇NS₂ = 848.09)P-70 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) P-71 m/z = 874.27(C₅₂H₃₈N₂O₂S =875.06) P-72 m/z = 872.29(C₅₃H₄₀N₂OS = 873O9) P-73 m/z =833.28(C₅₁H₃₉NOS = 834.05) P-74 m/z = 970.21(C₅₅H₃₈N₂OS₃ = 971.22) P-75m/z = 1055.33(C₇₆H₄₉NOS₂ = 1056.35) P-76 m/z = 741.27(C₅₅H₃₅NO₂ =741.89) P-77 m/z = 883.29(C₅₅H₄₁NOS = 884.11) P-78 m/z =931.31(C₆₉H₄₁NO₃ = 932.09) P-79 m/z = 868.31(C₅₄H₄₀N₂O₂ = 869O4) P-80m/z = 841.30(C₅₃H₃₉NO₂ = 842.01) P-81 m/z = 922.32(C₅₇H₄₂N₂O₃ = 923.08)P-82 m/z = 1124.40(C₈₃H₅₂N₂O₃ = 1125.34) P-83 m/z = 1164.43(C₈₅H₅₅N₂O₃ =1165.41) P-84 m/z = 1124.40(C₈₃H₅₂N₂O₃ = 1125.34) P-85 m/z =1014.33(C₇₃H₄₅N₂O₂S = 1015.24) P-86 m/z = 1154.35(C₈₃H₅₀N₂O₃S = 1155.38)P-87 m/z = 1115.41(C₈₁H₅₃N₃O₃ = 1116.33) P-88 m/z = 1140.43(C₈₄H₅₅N₂O₃ =1141.38) P-89 m/z = 1104.34(C₇₉H₄₈N₂O₃S = 1105.32) P-90 m/z =1074.38(C₇₉H₅₀N₂O₃ = 1075.28) P-91 m/z = 1038.38(C₇₆H₅₀N₂O₃ = 1039.25)P-92 m/z = 1235.38(C₈₇H₅₃N₃O₄S = 1236.46) P-93 m/z = 1154.35(C₈₃H₅₀N₂O₃S= 1155.38) P-94 m/z = 1196.40(C₈₅H₅₅N₂O₃S = 1197.47) P-95 m/z =1296.43(C₉₄H₅₀N₂O₃S = 1297.59) P-96 m/z = 1232.38(C₈₉H₅₅N₂OS₂ = 1233.56)P-97 m/z = 1196.35(C₈₅H₅₂N₂O₂S₂ = 1197.48) P-98 m/z =1154.35(C₈₃H₅₀N₂O₃S = 1155.38) P-99 m/z = 1443.45(C₁₀₂H₅₅N₃O₃S₂ =1444.78) P-100 m/z = 1190.44(C₈₈H₅₈N₂O₃ = 1191.44) P-101 m/z =938.30(C₅₇H₄₂N₂O₂S = 939.15) P-102 m/z = 1140.37(C₈₃H₅₂N₂O₂S = 1141.40)P-103 m/z = 1180.41(C₈₅H₅₅N₂O₂S = 1181.47) P-104 m/z =1216.41(C₈₉H₅₅N₂O₂S = 1217.50) P-105 m/z = 1030.31(C₇₃H₄₅N₂OS₂ =1031.30) P-106 m/z = 1170.33(C₈₃H₅₀N₂O₂S₂ = 1171.45) P-107 m/z =1131.39(C₈₁H₅₃N₃O₂S = 1132.39) P-108 m/z = 1188.36(C₈₄H₅₅N₂S₃ = 1189.57)P-109 m/z = 1120.32(C₇₉H₄₈N₂O₂S₂ = 1121.39) P-110 m/z =1090.36(C₇₉H₅₀N₂O₂S = 1091.34) P-111 m/z = 1070.34(C₇₅H₅₀N₂OS₂ =1071.37) P-112 m/z = 1251.35(C₈₇H₅₃N₃O₃S₂ = 1252.52) P-113 m/z =1170.33(C₈₃H₅₀N₂O₂S₂ = 1171.45) P-114 m/z = 1246.42(C₉₀H₅₈N₂O₃S =1247.53) P-115 m/z = 1346.45(C₉₈H₅₂N₂O₃S = 1347.65) P-116 m/z =1216.41(C₈₉H₅₅N₂O₂S = 1217.50) P-117 m/z = 1271.39(C₉₁H₅₇N₃OS₂ =1272.60) P-118 m/z = 1170.33(C₈₃H₅₀N₂O₂S₂ = 1171.45) P-119 m/z =1459.42(C₁₀₂H₅₅N₃O₂S₃ = 1460.84) P-120 m/z = 1206.42(C₈₈H₅₈N₂O₂S =1207.50) P-121 m/z = 1347.44(C₉₇H₅₁N₃O₃S = 1348.63) P-122 m/z =1579.48(C₁₁₃H₅₉N₃O₃S₂ = 1580.93) P-123 m/z = 1705.58(C₁₂₄H₇₉N₃O₄S =1707.07) P-124 m/z = 1489.47(C₁₀₇H₅₇N₃O₂S₂ = 1490.85) P-125 m/z =1453.43(C₁₀₃H₆₃N₃O₃S₂ = 1454.78) P-126 m/z = 1619.51(C₁₁₅H₇₃N₃O₃S₂ =1621.00) P-127 m/z = 1456.42(C₁₀₂H₆₄N₄OS₃ = 1457.84) P-128 m/z =1565.50(C₁₁₃H₇₁N₃O₂S₂ = 1566.95) P-129 m/z = 1528.48(C₁₀₉H₅₈N₄O₂S₂ =1529.89) P-130 m/z = 1519.42(C₁₀₇H₆₅N₃O₂S₃ = 1520.90) P-131 m/z =1826.61(C₁₃₁H₈₅N₄O₃S₂ = 1828.27) P-132 m/z = 1555.51(C₁₁₂H₇₃N₃O₂S₂ =1556.96) P-133 m/z = 1439.45(C₁₀₃H₆₅N₃O₂S₂ = 1440.79) P-134 m/z =1595.46(C₁₁₃H₆₉N₃O₂S₃ = 1596.99) P-135 m/z = 1721.56(C₁₂₄H₇₉N₃O₃S₂ =1723.13) P-136 m/z = 1571.44(C₁₁₁H₅₉N₃S₄ = 1573.03) P-137 m/z =1898.71(C₁₃₃H₁₀₂N₄O₃S₃ = 1900.48) P-138 m/z = 1812.54(C₁₂₉H₈₀N₄O₂S₃ =1814.27) P-139 m/z = 1914.69(C₁₃₃H₁₀₂N₄O₂S₄ = 1916.55) P1-1 m/z =705.27(C₅₂H₃₅NO₂ = 705.86) P1-2 m/z = 705.27(C₅₂H₃₅NO₂ = 705.86) P1-3m/z = 705.27(C₅₂H₃₅NO₂ = 705.86) P1-4 m/z = 705.27(C₅₂H₃₅NO₂ = 705.86)P1-5 m/z = 721.24(C₅₂H₃₅NOS = 721.92) P1-6 m/z = 829.30(C₅₂H₃₉NO₂ =830.00) P1-7 m/z = 829.30(C₅₂H₃₉NO₂ = 830.00) P1-8 m/z =829.30(C₅₂H₃₉NO₂ = 830.00) P1-9 m/z = 829.30(C₅₂H₃₉NO₂ = 830.00) P1-10m/z = 845.28(C₅₂H₃₉NOS = 846.06) P1-11 m/z = 827.28(C₅₂H₃₇NO₂ = 827.98)P1-12 m/z = 843.26(C₅₂H₃₇NOS = 844.04) P1-13 m/z = 781.30(C₅₈H₃₉NO₂ =781.96) P1-14 m/z = 797.28(C₅₈H₃₉NOS = 798.02) P1-15 m/z =781.30(C₅₈H₃₉NO₂ = 781.96) P1-16 m/z = 797.28(C₅₈H₃₉NOS = 798.02) P1-17m/z = 781.30(C₅₈H₃₉NO₂ = 781.96) P1-18 m/z = 797.28(C₅₈H₃₉NOS = 798.02)P1-19 m/z = 781.30(C₅₈H₃₉NO₂ = 781.96) P1-20 m/z = 781.30(C₅₈H₃₉NO₂ =781.96) P1-21 m/z = 781.30(C₅₈H₃₉NO₂ = 781.96) P1-22 m/z =781.30(C₅₈H₃₉NO₂ = 781.96) P1-23 m/z = 797.28(C₅₈H₃₉NOS = 798.02) P1-24m/z = 797.28(C₅₈H₃₉NOS = 798.02) P1-25 m/z = 797.28(C₅₈H₃₉NOS = 798.02)P1-26 m/z = 831.31(C₅₂H₄₁NO₂ = 832.02) P1-27 m/z = 847.29(C₅₂H₄₁NOS =848.08) P1-28 m/z = 831.31(C₅₂H₄₁NO₂ = 832.02) P1-29 m/z =847.29(C₅₂H₄₁NOS = 848.08) P1-30 m/z = 831.31(C₅₂H₄₁NO₂ = 832.02) P1-31m/z = 847.29(C₅₂H₄₁NOS = 848.08) P1-32 m/z = 782.29(C₅₇H₃₈N₂O₂ = 782.94)P1-33 m/z = 913.34(C₅₇H₄₇NOS = 914.18) P1-34 m/z = 855.31(C₆₄H₄₁NO₂ =856.04) P1-35 m/z = 849.30(C₅₂H₃₅D₄NOS = 850.08) P1-36 m/z =857.33(C₆₄H₄₃NO₂ = 858.05) P1-37 m/z = 873.31(C₅₄H₄₃NOS = 874.11) P1-38m/z = 857.33(C₆₄H₄₃NO₂ = 858.05) P1-39 m/z = 873.31(C₅₄H₄₃NOS = 874.11)P1-40 m/z = 873.31(C₅₄H₄₃NOS = 874.11) P1-41 m/z = 857.33(C₆₄H₄₃NO₂ =858.05) P1-42 m/z = 857.33(C₆₄H₄₃NO₂ = 858.05) P1-43 m/z =857.33(C₆₄H₄₃NO₂ = 858.05) P1-44 m/z = 873.31(C₅₄H₄₃NOS = 874.11) P1-45m/z = 873.31(C₆₄H₄₃NOS = 874.11) P1-46 m/z = 797.28(C₅₈H₃₉NOS = 798.02)P1-47 m/z = 721.24(C₅₂H₃₅NOS = 721.92) P1-48 m/z = 721.24(C₅₂H₃₅NOS =721.92) P1-49 m/z = 721.24(C₅₂H₃₅NOS = 721.92) P1-50 m/z =737.22(C₅₂H₃₅NS₂ = 737.98) P1-51 m/z = 845.28(C₅₂H₃₉NOS = 846.06) P1-52m/z = 861.25(C₅₂H₃₉NS₂ = 862.12) P1-53 m/z = 861.25(C₅₂H₃₉NS₂ = 862.12)P1-54 m/z = 861.25(C₅₂H₃₉NS₂ = 862.12) P1-55 m/z = 861.25(C₅₂H₃₉NS₂ =862.12) P1-56 m/z = 921.28(C₅₅H₃₉N₃OS = 922.12) P1-57 m/z =859.24(C₅₂H₃₇NS₂ = 860.11) P1-58 m/z = 797.28(C₅₈H₃₉NOS = 798.02) P1-59m/z = 813.25(C₅₈H₃₉NS₂ = 814.08) P1-60 m/z = 797.28(C₅₈H₃₉NOS = 798.02)P1-61 m/z = 813.25(C₅₈H₃₉NS₂ = 814.08) P1-62 m/z = 797.28(C₅₈H₃₉NOS =798.02) P1-63 m/z = 813.25(C₅₈H₃₉NS₂ = 814.08) P1-64 m/z =797.28(C₅₈H₃₉NOS = 798.02) P1-65 m/z = 813.25(C₅₈H₃₉NS₂ = 814.08) P1-66m/z = 847.29(C₅₂H₄₁NOS = 848.08) P1-67 m/z = 863.27(C₅₂H₄₁NS₂ = 864.14)P1-68 m/z = 847.29(C₅₂H₄₁NOS = 848.08) P1-69 m/z = 863.27(C₅₂H₄₁NS₂ =864.14) P1-70 m/z = 847.29(C₅₂H₄₁NOS = 848.08) P1-71 m/z =863.27(C₅₂H₄₁NS₂ = 864.14) P1-72 m/z = 798.27(C₅₇H₃₈N₂OS = 799.00) P1-73m/z = 797.28(C₅₈H₃₉NOS = 798.02) P1-74 m/z = 787.24(C₅₅H₃₇NS₂ = 788.04)P1-75 m/z = 787.24(C₅₅H₃₇NS₂ = 788.04) P1-76 m/z = 771.26(C₅₅H₃₇NOS =771.98) P1-77 m/z = 771.26(C₅₅H₃₇NOS = 771.98) P1-78 m/z =813.25(C₅₈H₃₉NS₂ = 814.08) P1-79 m/z = 907.35(C₆₈H₄₅NO₂ = 908.11) P1-80m/z = 903.31(C₅₈H₄₁NO₂ = 904.08) P1-81 m/z = 827.28(C₅₂H₃₇NO₂ = 827.98)P1-82 m/z = 843.26(C₅₂H₃₇NOS = 844.04) P1-83 m/z = 843.26(C₅₂H₃₇NOS =844.04) P1-84 m/z = 787.24(C₅₅H₃₇NS₂ = 788.04) P1-85 m/z =879.31(C₅₅H₄₁NO₂ = 880.06) P1-86 m/z = 781.30(C₅₈H₃₉NO₂ = 781.96) P2-1m/z = 843.28(C₅₂H₃₇NO₃ = 843.98) P2-2 m/z = 843.28(C₅₂H₃₇NO₃ = 843.98)P2-3 m/z = 843.28(C₅₂H₃₇NO₃ = 843.98) P2-4 m/z = 843.28(C₅₂H₃₇NO₃ =843.98) P2-5 m/z = 909.27(C₅₅H₃₉NO₂S = 910.10) P2-6 m/z =861.27(C₅₂H₃₅FNO₃ = 861.97) P2-7 m/z = 893.29(C₅₅H₃₉NO₃ = 894.04) P2-8m/z = 995.34(C₇₄H₄₅NO₃ = 996.18) P2-9 m/z = 859.25(C₆₂H₃₇NO₂S = 860.04)P2-10 m/z = 859.25(C₆₂H₃₇NO₂S = 860.04) P2-11 m/z = 859.25(C₅₂H₃₇NO₂S =860.04) P2-12 m/z = 859.25(C₅₂H₃₇NO₂S = 860.04) P2-13 m/z =859.25(C₅₂H₃₇NO₂S = 860.04) P2-14 m/z = 859.25(C₅₂H₃₇NO₂S = 860.04)P2-15 m/z = 859.25(C₆₂H₃₇NO₂S = 860.04) P2-16 m/z = 859.25(C₆₂H₃₇NO₂S =860.04) P2-17 m/z = 875.23(C₅₂H₃₇NOS₂ = 876.10) P2-18 m/z =875.23(C₅₂H₃₇NOS₂ = 876.1) P2-19 m/z = 891.21(C₅₂H₃₇NS₃ = 892.17) P2-20m/z = 919.31(C₅₈H₄₁NO₃ = 920.08) P2-21 m/z = 935.29(C₅₈H₄₁NO₂S = 936.14)P2-22 m/z = 951.26(C₅₈H₄₁NOS₂ = 952.20) P2-23 m/z = 967.24(C₅₈H₄₁NS₃ =968.26) P2-24 m/z = 985.30(C₇₂H₄₃NO₂S = 986.20) P2-25 m/z =1001.28(C₇₂H₄₃NOS₂ = 1002.26) P2-26 m/z = 952.26(C₅₇H₄₀N₂OS₂ = 953.19)P2-27 m/z = 952.26(C₆₇H₄₀N₂OS₂ = 953.19) P2-28 m/z = 919.31(C₅₈H₄₁NO₃ =920.08) P2-29 m/z = 935.29(C₅₈H₄₁NO₂S = 936.14) P2-30 m/z =919.31(C₅₈H₄₁NO₃ = 920.08) P2-31 m/z = 935.29(C₅₈H₄₁NO₂S = 936.14) P2-32m/z = 935.29(C₅₈H₄₁NO₂S = 936.14) P2-33 m/z = 967.24(C₅₈H₄₁NS₃ = 968.26)P2-34 m/z = 900.23(C₅₃H₃₅N₂OS₂ = 901.11) P2-35 m/z = 901.25(C₅₄H₃₉NOS₂ =902.14) P2-36 m/z = 893.29(C₅₅H₃₉NO₃ = 894.04) P2-37 m/z =941.22(C₅₅H₃₉NS₃ = 942.23) P2-38 m/z = 909.27(C₅₅H₃₉N0₂S = 910.10) P2-39m/z = 919.31(C₅₈H₄₁NO₃ = 920.08) P2-40 m/z = 941.22(C₅₅H₃₉NS₃ = 942.23)P2-41 m/z = 909.27(C₅₅H₃₉NO₂S = 910.1) P2-42 m/z = 893.29(C₅₅H₃₉NO₃ =894.04) P2-43 m/z = 941.22(C₅₅H₃₉NS₃ = 942.23) P2-44 m/z =909.27(C₅₅H₃₉NO₂S = 910.10) P2-45 m/z = 893.29(C₅₅H₃₉NO₃ = 894.04) P2-46m/z = 951.26(C₅₈H₄₁NOS₂ = 952.2) P2-47 m/z = 1017.26(C₇₂H₄₃NS₃ =1018.32) P2-48 m/z = 995.34(C₇₄H₄₅NO₃ = 996.18) P2-49 m/z =895.23(C₅₂H₃₃D₄NS₃ = 896.19) P2-50 m/z = 995.34(C₇₄H₄₅NO₃ = 996.18)P2-51 m/z = 995.34(C₇₄H₄₅NO₃ = 996.18) P2-52 m/z = 1093.29(C₇₈H₄₇NS₃ =1094.42) P2-53 m/z = 975.26(C₇₀H₄₁NOS₂ = 976.22) P2-54 m/z =991.24(C₇₀H₄₁NS₃ = 992.29) P2-55 m/z = 943.31(C₇₀H₄₁NO₃ = 944.10)

Evaluation of Manufacture of Organic Electronic Element [Example 1] RedOrganic Light Emitting Diode (Emitting Auxiliary Layer)

An organic light emitting diode was manufactured according to aconventional method using the compound of the present invention as anemitting auxiliary layer material. First, a hole injection layer wasformed by vacuum depositing4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,2-TNATA) to a thickness of 60 nm on an ITO layer (anode) formed on aglass substrate, and a hole transport layer was formed by vacuumdeposition ofN,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1-biphenyl)-4,4′-diamine(hereinafter, NPB) to a thickness of 60 nm on the hole injection layer.Subsequently, compound PA-1 was vacuum-deposited to a thickness of 20 nmon the hole transport layer to form an emission auxiliary layer,4,4′-N,N′-dicarbazole-biphenyl (hereinafter, CBP) was used as a hostmaterial and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate(hereinafter, (piq)2lr(acac)) was used as a dopant material on theemitting auxiliary layer, doped at a weight ratio of 95:5, and vacuumdeposited to a thickness of 30 nm to form an emitting layer.

Subsequently,(1,1-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, BAlq) was vacuum deposited to a thickness of 10 nm on theemitting layer to form a hole blocking layer, an electron transportlayer was formed by vacuum depositing tris-(8-hydroxyquinoline)aluminum(hereinafter, Alq₃) to a thickness of 40 nm on the hole blocking layer.Thereafter, an electron injection layer was formed by depositing LiF, analkali metal halide, to a thickness of 0.2 nm, then, Al was deposited toa thickness of 150 nm to form a cathode, thereby manufacturing anorganic light emitting diode.

[Example 2] to [Example 21] Red Organic Light Emitting Diode (EmittingAuxiliary Layer)

An organic light emitting diode was manufactured in the same manner asin Example 1, except that the compound PA-2 and the compound of thepresent invention described in Table 4 below were used instead of thecompound PA-1 as the emitting auxiliary layer material.

Comparative Example 1

An organic light emitting diode was manufactured in the same manner asin Example 1, except that the comparative example 1 below were usedinstead of the compound PA-1 as the emitting auxiliary layer material.

Electroluminescence (EL) characteristics were measured by PR-650 ofphotoresearch company by applying a forward bias direct current voltageto the organic light emitting diodes prepared according to Examples 1 to21 and Comparative Example 1 of the present invention, T95 life wasmeasured through a life measurement equipment manufactured by McScienceat a luminance of 2500 cd/m², and the measurement results are shown inTable 4 below.

TABLE 4 Voltage Current Density Brightness Efficiency Lifetime CIEcompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comparative Comparative6.3 26.6 2500.0 9.4 75.6 0.64 0.31 example(1) compound 1 example(1) PA-16.0 21.9 2500.0 11.4 98.3 0.63 0.35 example(2) PA-2 5.6 18.1 2500.0 13.8110.5 0.61 0.31 example(3) P-1 4.8 11.1 2500.0 22.6 116.4 0.64 0.30example(4) P-4 4.9 10.3 2500.0 24.3 112.7 0.63 0.31 example(5) P-12 4.89.7 2500.0 25.7 118.3 0.62 0.30 example(6) P-14 4.9 9.7 2500.0 25.9117.2 0.61 0.31 example(7) P-22 4.8 9.7 2500.0 25.7 119.0 0.64 0.30example(8) P-30 5.0 10.7 2500.0 23.5 113.4 0.65 0.35 example(9) P-37 4.910.8 2500.0 23.2 116.9 0.62 0.33 example(10) P-57 5.2 10.9 2500.0 22.9112.0 0.64 0.32 example(11) P-59 5.2 9.7 2500.0 25.9 115.4 0.61 0.30example(12) P-68 5.2 10.6 2500.0 23.6 114.7 0.64 0.30 example(13) P-775.1 10.3 2500.0 24.4 119.5 0.61 0.30 example(14) P-81 5.0 11.6 2500.021.6 122.8 0.62 0.30 example(15) P-82 5.2 11.9 2500.0 21.1 120.7 0.630.30 example(16) P-94 5.1 11.5 2500.0 21.8 120.9 0.65 0.32 example(17)P-109 5.0 11.6 2500.0 21.5 120.8 0.63 0.35 example(18) P-115 5.2 11.12500.0 22.6 123.9 0.62 0.31 example(19) P-124 5.3 12.0 2500.0 20.8 124.10.60 0.34 example(20) P-136 5.3 12.3 2500.0 20.3 126.7 0.63 0.34example(21) P-138 5.3 12.4 2500.0 20.2 127.3 0.64 0.35

As can be seen from the results in Table 4, when a red organic lightemitting diode is manufactured using the material for an organic lightemitting diode of the present invention as a phosphorescent hostmaterial, compared to the case of using the compound PA-1, the compoundPA-2, and the comparative compound 1, the driving voltage of the organiclight emitting diode could be lowered and the efficiency and lifespanwere significantly improved.

In detail, the comparative compound and the compound of the presentinvention are the same in that they contain a xanthene core and an aminesubstituent, the device result of compound PA-1 substituted withdibenzofuran was improved compared to Comparative Compound 1 in which asimple aryl group was substituted with the substituent of the aminegroup, and the device result of compound PA-2 with more secondarysubstituents bonded was more improved. Also, the compound PA-2 and thecompound of the present invention differ in the bonding position of thesecondary substituent of the amine substituent, dibenzofuran ordibenzothiophene. In other words, it was confirmed that the compound ofthe present invention, in which an amine group and a secondarysubstituent group are bonded to the same ring in dibenzofuran ordibenzothiophene, exhibits more improved device performance thancompound PA-2.

This result shows that the difference in hole mobility is largedepending on the bonding position of the substituent, and thisdifference in mobility affects the overall device.

By using the compound of the present invention as an emitting auxiliarylayer, the HOMO or LUMO energy level of the compound of the presentinvention has an appropriate value between the hole transport layer andthe emitting layer, as a result, holes and electrons achieve a chargebalance, and light emission occurs inside the emitting layer rather thanat the interface of the hole transport layer, maximizing efficiency andlifespan.

Meanwhile, comparing the results of the embodiments of the presentinvention, it can be seen that there are differences in driving voltageand luminous efficiency according to the bonding position and type ofthe secondary substituent, and different lifespan results are produceddepending on the number of substitutions of amino groups in the centralcore.

In conclusion, the physical properties of the compound such as holecharacteristics, light efficiency characteristics, energy level (LUMO,HOMO level, T1 level), hole injection & mobility characteristics, andelectron blocking characteristics vary depending on the substituent,resulting in completely different device results.

[Example 22] Green Organic Light Emitting Diode (Emitting AuxiliaryLayer)

2-TNATA was vacuum-deposited to a thickness of 60 nm on the ITO layer(anode) formed on the glass substrate to form a hole injection layer,and then NPB was vacuum-deposited to a thickness of 60 nm on the holeinjection layer to form a hole transport layer. Subsequently, thefollowing compound PA-3 was vacuum-deposited to a thickness of 20 nm onthe hole transport layer to form an emitting auxiliary layer, and on theemitting auxiliary layer, CBP was used as a host material andtris(2-phenylpyridine)-iridium (hereinafter, Ir(ppy)₃) was used as adopant material, doped at a weight ratio of 95:5, and vacuum depositedto a thickness of 30 nm to form an emitting layer. Then, BAlq wasvacuum-deposited to a thickness of 10 nm on the emitting layer to form ahole blocking layer, Alq₃ was vacuum deposited on the hole blockinglayer to a thickness of 40 nm on the hole blocking layer to form anelectron transport layer. Thereafter, an electron injection layer wasformed by depositing LiF, an alkali metal halide, to a thickness of 0.2nm, and subsequently, Al was deposited to a thickness of 150 nm to forma cathode, thereby manufacturing an organic light emitting diode.

[Example 23] to [Example 35] Green Organic Light Emitting Diode(Emitting Auxiliary Layer)

An organic light emitting diode was manufactured in the same manner asin Example 22, except that the compound of the present inventiondescribed in Table 5 below was used instead of the compound PA-3 as theemitting auxiliary layer material.

[Comparative Example 2] and [Comparative Example 3]

An organic light emitting diode was manufactured in the same manner asin Example 22, except that Comparative Compound 2 and ComparativeCompound 3 were used, respectively, instead of the compound PA-3 as theemitting auxiliary layer material.

Electroluminescence (EL) characteristics were measured by PR-650 ofphotoresearch company by applying a forward bias direct current voltageto the organic light emitting diode prepared according to Examples 22 to35 and Comparative Example 2 to 3 of the present invention, T95 life wasmeasured through a life measurement equipment manufactured by McScienceat a luminance of 5000 cd/m², and the measurement results are shown inTable 5 below.

TABLE 5 Voltage Current Density Brightness Efficiency Lifetime CIEcompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comparative comparative6.3 36.2 5000.0 13.8 75.6 0.30 0.61 example (2) compound 2 comparativecomparative 6.1 25.6 5000.0 19.5 75.9 0.30 0.60 example (3) compound 3example(22) PA-3 5.6 24.5 5000.0 20.4 103.3 0.32 0.65 example(23) P1-25.0 10.1 5000.0 49.7 139.6 0.32 0.62 example(24) P1-5 5.2 12.7 5000.039.4 129.3 0.32 0.61 example(25) P1-6 5.1 11.7 5000.0 42.9 135.6 0.330.60 example(26) P1-12 5.2 12.6 5000.0 39.6 130.5 0.31 0.64 example(27)P1-20 5.2 12.4 5000.0 40.2 129.5 0.33 0.61 example(28) P1-44 5.1 11.45000.0 43.9 137.0 0.31 0.60 example(29) P1-50 5.1 12.6 5000.0 39.5 129.70.30 0.62 example(30) P1-55 5.1 10.6 5000.0 47.2 137.3 0.31 0.64example(31) P1-73 5.0 12.1 5000.0 41.2 136.2 0.33 0.61 example(32) P1-775.3 11.3 5000.0 44.3 129.7 0.35 0.61 example(33) P1-78 5.0 11.9 5000.042.2 132.6 0.32 0.61 example(34) P1-84 5.3 13.8 5000.0 36.2 127.3 0.330.62 example(35) P1-85 5.3 14.1 5000.0 35.5 127.6 0.32 0.63

As can be seen from the results in Table 5, when a green organic lightemitting diode is manufactured using the material for an organic lightemitting diode of the present invention as an emitting auxiliary layermaterial, compared to the case of using the comparative compound 2, thecomparative compound 3, the compound PA-3, and the driving voltage ofthe organic light emitting diode could be lowered and the efficiency andlifespan were significantly improved.

Specifically, in the case of a comparative compound, the device resultsusing Comparative Compound 3 with arylamine bonded at the 2 position ofthe xanthene core, compared to Comparative Compound 2 with arylaminebonded at the 3 position of the xanthene core, improved efficiency.Also, it can be seen that the device result of the compound PA-3 inwhich a heterocyclic compound such as dibenzofuran is bonded as asubstituent of an amine group is improved as a whole.

The compound of the present invention is a compound characterized inthat an amine group is bonded to 2 position of the xanthene core, anddibenzofuran or 1 substituted dibenzothiophene is bonded as asubstituent of the amine group bonded to the core, it can be seen thatthe device results of Examples 23 to 35 made of the compounds of thepresent invention having such characteristics are remarkably excellent.

These results can be explained by the HOMO values of ComparativeCompound 2, Comparative Compound 3, Compound PA-3, and the presentcompound. Referring to Table 6 below, it can be seen that the HOMO valueof Comparative Compound 3 in which an amine group is bonded at the 2position of the core is higher than Comparative Compound 2 in which anamine group is bonded at the 3 position of the core. Also, it can beseen that the HOMO value of Compound P-14 of the present invention inwhich the amine group is bonded to the 2 position of the core and 1substituted dibenzofuran is bonded as a substituent of the bonded aminegroup is the highest, compared to the compound PA-3 in which an aminegroup is bonded to the 3 position of the core and 3 substituteddibenzofuran is bonded as a substituent of the bonded amine group.

TABLE 6 comparative comparative compound 2 compound 3 PA-3 P-14 HOMO(eV) −4.956 −4.808 −4.844 −4.781

That is, it is shown that the compound of the present inventionfacilitates hole injection compared to the comparative compounds,thereby improving hole mobility, thereby improving the driving voltage,efficiency, and lifespan of the entire element.

In conclusion, even if the core is the same compound, the physicalproperties of the compound such as hole characteristics, lightefficiency characteristics, energy level (LUMO, HOMO level, T1 level),hole injection & mobility characteristics, and electron blockingcharacteristics vary depending on the bonding position of thesubstituent, resulting in completely different element results.

[Example 36] Green Organic Light Emitting Diode (Emitting AuxiliaryLayer)

2-TNATA was vacuum-deposited to a thickness of 60 nm on the ITO layer(anode) formed on the glass substrate to form a hole injection layer,and then NPB was vacuum-deposited to a thickness of 60 nm on the holeinjection layer to form a hole transport layer. Then, after vacuumdeposition of the compound P 2-1 of the present invention to a thicknessof 20 nm on the hole transport layer to form an emitting auxiliarylayer, and on the emitting auxiliary layer, CBP was used as a hostmaterial and tris(2-phenylpyridine)-iridium(hereinafter, Ir(ppy)₃) wasused as a dopant material, doped at a weight ratio of 95:5, and vacuumdeposited to a thickness of 30 nm to form an emitting layer.Subsequently, BAlq was vacuum deposited to a thickness of 10 nm on theemitting layer to form a hole blocking layer,Bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, BeBq₂) wasvacuum deposited to a thickness of 40 nm on the hole blocking layer toform an electron transport layer. Thereafter, an electron injectionlayer was formed by depositing LiF, an alkali metal halide, to athickness of 0.2 nm, and subsequently, Al was deposited to a thicknessof 150 nm to form a cathode, thereby manufacturing an organic lightemitting diode.

[Example 37] to [Example 47] Green Organic Light Emitting Diode(Emitting Auxiliary Layer)

An organic light emitting diode was manufactured in the same manner asin Example 36, except that the compound of the present inventiondescribed in Table 7 below was used instead of the compound P2-1 as theemitting auxiliary layer material.

[Comparative Example 4] to [Comparative Example 6]

An organic light emitting diode was manufactured in the same manner asin Example 36, except that Comparative Compound 2 and ComparativeCompound 4 were used, respectively, instead of the compound P2-1 as theemitting auxiliary layer material.

Electroluminescence (EL) characteristics were measured by PR-650 ofphotoresearch company by applying a forward bias direct current voltageto the organic light emitting diode prepared according to Examples 36 to47 and Comparative Example 4 to 6 of the present invention, T95 life wasmeasured through a life measurement equipment manufactured by McScienceat a luminance of 5000 cd/m², and the measurement results are shown inTable 7 below.

TABLE 7 Voltage Current Density Brightness Efficiency Lifetime CIEcompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comparative comparative6.5 33.1 5000.0 15.1 80.4 0.32 0.64 example (4) compound 2 comparativecomparative 6.3 24.9 5000.0 20.1 88.6 0.30 0.64 example (5) compound 3comparative comparative 5.9 19.3 5000.0 25.9 105.7 0.32 0.63 example (6)compound 4 example(36) P2-1 5.1 10.6 5000.0 47.2 133.2 0.33 0.60example(37) P2-3 5.1 10.3 5000.0 48.4 135.1 0.33 0.61 example(38) P2-75.3 11.2 5000.0 44.5 128.7 0.34 0.60 example(39) P2-12 5.2 10.7 5000.046.7 122.6 0.30 0.62 example(40) P2-14 5.1 11.3 5000.0 44.2 127.1 0.320.60 example(41) P2-22 5.1 11.2 5000.0 44.7 122.5 0.30 0.62 example(42)P2-28 5.2 10.8 5000.0 46.4 132.5 0.34 0.65 example(43) P2-37 5.4 12.85000.0 39.0 120.2 0.34 0.60 example(44) P2-39 5.3 12.7 5000.0 39.3 131.50.32 0.64 example(45) P2-40 5.4 12.9 5000.0 38.8 120.8 0.34 0.61example(46) P2-46 5.3 11.1 5000.0 45.0 124.2 0.31 0.62 example(47) P2-505.2 12.2 5000.0 41.0 126.6 0.31 0.62

As can be seen from the results in Table 7, when a green organic lightemitting diode is manufactured using the material for an organic lightemitting diode of the present invention as an emitting auxiliary layermaterial, compared to the comparative compound 4 to 6, and the drivingvoltage of the organic light emitting diode could be lowered and theefficiency and lifespan were significantly improved.

First, the device result using Comparative Compound 3 with arylaminebonded at the 2 position of the xanthene core was slightly improved thanComparative Compound 2 with arylamine bonded at the 3 position of thexanthene core, and the device result of Comparative Compound 4 in whichone more xanthene was bonded as a substituent of the amine group wasimproved compared to Comparative Examples 4 and 5.

The compound of the present invention is a compound characterized inthat an amine group is bonded to 2 position of the xanthene core, and asa substituent of the amine group bonded to the core, one is bonded with1 position of the dibenzofuran or dibenzothiophene, and the other isbonded with xanthene one more, and it can be seen that the deviceresults of Examples 36 to 47 made of the compounds of the presentinvention having such characteristics are remarkably excellent.

This is as described in Table 5 above, it is suggested that thecompounds of the present invention having a substituent at a specificbonding site may have significantly different chemical and physicalproperties from those of the Comparative Example compounds, therebyleading to improved device results.

Additionally, referring to Table 8 below, which lists the HOMO values ofComparative Compound 4 and the compound of the present invention, it canbe seen that the HOMO value of Compound P 2-3 of the present invention,in which an amine group is bonded to the 2 position of the core, and onemore xanthene is bonded at the same time as 1 position of dibenzofuranas a substituent of the bonded amine group, is higher than that ofComparative Compound 4.

TABLE 8 Comparative compound 4 P2-3 HOMO (eV) −4.856 −4.788

That is, it is judged that the compound of the present invention canmore efficiently transport holes in the hole transport layer, as aresult, it is believed that the charge balance of holes and electrons inthe emitting layer is increased, thereby improving the driving voltage,efficiency, and lifespan of the entire device.

In the case of the emitting auxiliary layer, it is necessary to graspthe correlation between the hole transport layer and the emitting layer(host), even if a similar core is used, it will be very difficult for aperson skilled in the art to infer the characteristics exhibited in theemitting auxiliary layer in which the compound of the present inventionis used.

In addition, the device characteristics in which the compound of thepresent invention was applied to only one of the emitting auxiliarylayers were described in the result of evaluation of manufacture of theelement above, but it may be applied to a case where a hole transportlayer or both a hole transport layer and an emitting auxiliary layer areformed by using the compound of the present invention.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis ofthe accompanying claims, and it shall be construed that all of thetechnical ideas included within the scope equivalent to the claimsbelong to the present invention.

BRIEF DESCRIPTION OF THE DRAWINGS 100, 200, 300: organic electronicelement 110: the first electrode 120: hole injection layer 130: holetransport layer 140: emitting layer 150: electron transport layer 160:electron injection layer 170: second electrode 180: light efficiencyenhancing Layer 210: buffer layer 220: emitting-auxiliary layer 320:first hole injection layer 330: first hole transport layer 340: firstemitting layer 350: first electron transport 360: first chargegeneration layer layer 361: second charge generation 420: second holeinjection layer layer 430: second hole transport layer 440: secondemitting layer 450: second electron transport layer CGL: chargegeneration layer ST1: first stack ST1: second stack

1. A compound represented by Formula 6-1:

wherein: 1) X¹ and X³ are each independently O or S, 2) e, g, h, j, r, sand t are each independently an integer of 0 to 4, and f and q are aninteger of 0 to 3, wherein in case e, f, g, h, j, q, r, s and t are 2 ormore, R¹, R², R³, R⁴, R⁶, R⁹, R¹⁰, R¹¹ and R¹² are each in plural beingthe same or different, and an adjacent plurality of R¹ or a plurality ofR² or a plurality of R³ or a plurality of R⁴ or a plurality of R⁶ or aplurality of R⁹ or a plurality of R¹⁰ or a plurality of R¹¹ or aplurality of R¹² may be bonded to each other to form a ring, 3) n is aninteger of 0 to 3, 4) L³, L⁴ and L⁹ are the same or different from eachother, and are each independently selected from the group consisting ofsingle bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₂-C₆₀heterocyclic group; 5) Ar³ is selected from the group consisting ofhydrogen; deuterium; tritium; halogen; cyano group; nitro group; C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including atleast one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀alkenyl group; C₂-C₂₀ alkynyl group; C₁-C₃₀ alkoxyl group; C₆-C₃₀aryloxy group; and -L′-N(R_(a))(R_(b)); 6) R¹, R², R³, R⁴, R⁶, R⁹, R¹⁰,R¹¹ and R¹² are the same or different from each other, and are eachindependently selected from the group consisting of hydrogen; deuterium;tritium; halogen; cyano group; nitro group; C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; C₁-C₅₀ alkyl group; C₂-C₂₀ alkenylgroup; C₂-C₂₀ alkynyl group; C₁-C₃₀ alkoxyl group; C₆-C₃₀ aryloxy group;and -L′-N(R_(a))(R_(b)); 7) wherein L′ is selected from the groupconsisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylenegroup; C₃-C₆₀ aliphatic ring; a C₂-C₆₀ heterocyclic group including atleast one heteroatom of O, N, S, Si or P; a combination thereof; whereinR_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; C₃-C₆₀ aliphaticring; a C₂-C₆₀ heterocyclic group including at least one heteroatom ofO, N, S, Si or P; 8) Y¹ is O or S, 9) wherein, the aryl group, arylenegroup, heterocyclic group, fluorenyl group, fluorenylene group, fusedring group, alkyl group, alkenyl group, alkoxy group and aryloxy groupmay be substituted with one or more substituents selected from the groupconsisting of deuterium; halogen; silane group; siloxane group; borongroup; germanium group; cyano group; nitro group; C₁-C₂₀ alkylthiogroup; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group;C₂-C₂₀ alkynyl group; C₆-C₂₅ aryl group; C₆-C₂₅ aryl group substitutedwith deuterium; a fluorenyl group; C₂˜C₂₀ heterocyclic group; C₃-C₂₀cycloalkyl group; C₇-C₂₀ arylalkyl group; C₈-C₂₀ arylalkenyl group; and-L′-N(R_(a))(R_(b)); the substituents may combine each other to form asaturated or unsaturated ring selected from the group consisting of aC₃-C₆₀ aliphatic ring, a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclicgroup, a fused ring formed by combination thereof.
 2. The compoundaccording to claim 1, wherein Formula 6-1 is represented by Formula 6-2:

wherein X¹, X³, Y¹, R¹, R², R³, R⁴, R⁶, R⁹, R¹⁹, R¹¹, R¹², L³, L⁴, Ar³,e, f, g, h, j, n, q, r, s, and t are the same as defined in claim
 1. 3.The compound according to claim 1, wherein Formula 6-1 is represented byFormula 6-3:

wherein X¹, X³, Y¹, R¹, R², R³, R⁴, R⁶, R⁹, R¹⁹, R¹¹, R¹², L³, L⁴, Ar³,e, f, g, h, j, n, q, r, s, and t are the same as defined in claim
 1. 4.The compound according to claim 1, wherein Formula 6-1 is represented byany one of the following compounds:


5. An organic electronic element comprising an anode, a cathode, and anorganic material layer formed between the anode and the cathode, whereinthe organic material layer comprises a single compound or 2 or morecompounds represented by Formula 6-1 of claim
 1. 6. The organicelectronic element of claim 5, wherein the organic material layercomprises at least one of a hole injection layer, a hole transportlayer, an emitting auxiliary layer, an emitting layer, an electrontransport auxiliary layer, an electron transport layer, and an electroninjection layer.
 7. The organic electronic element of claim 5, whereinthe organic material layer is an emitting auxiliary layer.
 8. Theorganic electronic element of claim 5, further comprising a lightefficiency enhancing layer formed on at least one surface of the anodeand the cathode, the surface being on the opposite side of the organicmaterial layer, not in contact with the organic material layer.
 9. Theorganic electronic element of claim 5, wherein the organic materiallayer comprises 2 or more stacks including a hole transport layer, anemitting layer, and an electron transport layer sequentially formed onthe anode.
 10. The organic electronic element of claim 9, wherein theorganic material layer further comprises a charge generation layerformed between the 2 or more stacks.
 11. A display device comprising theorganic electronic element of claim 5; and a control unit for drivingthe display device.
 12. The display device according to claim 11,wherein the organic electronic element is at least one of an OLED, anorganic solar cell, an organic photo conductor(OPC), organictransistor(organic TFT) and an element for monochromic or whiteillumination.